Disclaimer: This is a work of fiction, and any resemblance to real people is purely coincidental. It is also a work intended for adults, and it involves sex between men, women, and young adult men. If you are offended by material of this kind, or if it is illegal in your political jurisdiction to read material of this kind, please exit immediately. This story is posted to the Nifty Archives, and it may be read and downloaded for the pleasure of individuals. It may not be posted to any other media outlet without the written consent of its author. The author appreciates comments from readers.
Nick's Adventures in the Caribbean Part Two
The flight to Key West went smoothly, but I was a little nervous in the four-seater plane. It was just like the one my parents crashed in. I didn't say anything to Tom, of course, and I made it through okay. We were allowed to smoke, and that helped.
We met Jerry at the airport, just as planned. He was a pretty nice looking kid, although he was a little on the skinny side. He was about 5'8'', the same size as Tom, and I took a certain adolescent pleasure in being the biggest one in the group. We got a taxi to the marina where the boat was docked. Tom had made arrangements for it to be ready to sail as soon as we got there, so we didn't waste any time getting ready to shove off. We motored out of the marina, and we hoisted sail just off the island.
To Tom's surprise, Jerry knew something about sailing, so he gave him more help than he expected. I pitched in when I was needed. By the time we were five miles off shore, Tom was ready to strip down.
"I don't know about you guys, but these clothes are starting to chap my ass. I'm getting naked, and I suggest you do the same."
"I'm with you," I said, and I shucked my tank top and shorts. I kept my sandals on, though, to keep from burning my feet on the deck. Tom and I both watched Jay's--that's what he preferred to be called--reaction. He didn't join us. Instead, he kind of stared at each of us in turn. The rest of that day and on into the night, I caught him checking out my package every time he thought I wouldn't notice.
Around five we anchored off a tiny island off the coast of Cuba that was uninhabited. Tom and I got the scuba gear out and went for a dive. Jay said he wanted to learn how, but he wasn't a diver yet. Tom promised to teach him. The water was pretty good, and we saw some pretty amazing coral formations. There were millions of multi-colored fish everywhere.
I decided to get out to spend a little time alone with Jay. When I got out of the water, my cock was distended to its full nine inches, but it wasn't really hard. It hung down as it usually does soft, but it definitely had body to it. Jay's eyes almost popped out of his head when he saw that. He started to say something, and then thought better of it.
I lay on the deck next to him. Sunset was pretty close at hand, and the view was spectacular. I went and got my camera and took a couple of shots. Jay asked to see it, so I handed it to him. He was pretty impressed by it. Then he did something I didn't expect. He aimed the lens at me an took a picture. I didn't mind, but he was so modest that I was surprised he wanted to shoot me naked with a semi.
I lay back down and draped my cock over my thigh on his side. All day I had watched the little spot of pre-cum on his shorts get bigger and bigger, and I wanted to see if he would do anything. We talked about him, mostly. He had just graduated from a Catholic high school in Miami. A lot of his friends were Cubans, so he spoke Spanish pretty well, he said. I shifted to Spanish, and he was impressed. He answered me in Spanish, but it was rather naive and childish. He really didn't speak "adult" Spanish.
"So, do you play any sports," I asked.
"Not really. I was on the computer team at school, though."
"Oh, yeah? Tell me about it." The term "nerd" came to my mind immediately, but I just pretended that the computer team and the football team were of equal status.
He told me all about his computer team, which was exactly like the computer team at Colton. They went to competitions and wrote programs. The team that did the best program in the shortest time won. His team had finished sixth in the state that spring.
I lit a cigarette and offered him one. He looked like he was about to take it but changed his mind. I could tell this kid was really confused about what was going on around him.
"How long have you known Tom," he asked.
"Not long, really. A few weeks." That was a lie, of course, but it just seemed like the right thing to say.
"He's my father, you know," he said. "Well, really, he's just my biological father. My mom's husband adopted me when I was two, and I consider him my father, not Tom."
"Well, if he raised you, he is your father," I said. "How come he couldn't take care of you?"
"He's dead. He was Cuban, and he was a pilot for an organization called Brothers to the Rescue. His plane was shot down two years ago. The government calls it an accidental crash, but we know he was shot down."
"I'm sorry, man. That gives us something in common, though. Both my parents, and my dad's only brother, were killed in a plane crash last November."
"I'm sorry, too, Nick." He put his hand on my arm, and I did a pretty mean thing: I tightened all the muscles in my groin and made my cock jump. He snatched his arm away instantly. "Sorry," he said.
"For what," I asked.
"For. . .for everything. For your parents, I mean."
Tom surfaced just about then, and his cock was standing out at a ninety degree angle. It wasn't a sexual hard-on; it was just a distended cock, like I had. He paid no attention to it, but the bulge Jay had been sporting since I came up got bigger.
I had drawn first round of galley rotation, so I got up to start cooking. Most of the food on board was frozen and ready for the microwave. I had eaten this kind of stuff before. It was all pretty tasty, and some of it was really good. I made drinks for all three of us and brought them out on deck while the microwave was working its magic.
We lounged on the deck in large, comfortable chairs. It would take forty minutes for all of our dinners to defrost and warm up enough to eat. Tom and I drank and smoked, and we generally shot the shit about the day. After we ate, we sat out some more and enjoyed the coolness of the sea breeze that swept over us. We had a few more drinks, and I think they kind of got to Jay. Around nine he went to bed.
Tom and I stayed out on deck. After we thought Jay had surely fallen asleep, we put the moves on one another. Tom started by sucking my cock, and I moved him down into the 69 position. After we both came and rested a while, I started sucking Tom's ass, moving my tongue as far into him as I could. When he was ready, I mounted him and fucked him for a long, long time. We both let out loud moans of contentment when we came. We lay in place for a long time, snuggling and caressing each other. We had turned out all but the safety lights, and I marvelled at the millions of stars that were visible. The air was cool, and the warmth between us felt good.
After a long time, Tom spoke: "Did you and Jer. . .er, Jay have a chance to talk?"
"A little. He doesn't consider you his father. Apparently his mother's second husband adopted him, and he considers him his father. He's dead, though."
"I knew he had been adopted because I had to sign away any parental rights. I think I also knew he was dead."
"Did you see his reaction when we stripped," I asked.
"I damn sure did. I noticed the boner he wore most of the day, too. I'll start teaching him something about diving tomorrow, if he's still interested."
I had to take a leak, so I got up and walked to the side of the boat to piss in the ocean. Tom joined me. He wanted to hold my cock as I pissed, so I let him. I had my legs apart to piss, and he moved behind me, his left leg between mine. His cock was half hard, and he rested it on my thigh. After I was through pissing, he put his left arm around me and found my right nipple. He started kneading it and rubbing my cock at the same time. I got hard quickly, and that seemed to make him stiffen, as well. He continued jerking my cock and moving back and forth against me so his cock was stimulated, as well. We both came in a terrific climax that almost made us lose balance. "Let's go to bed," he whispered. We went below deck into the larger cabin and slept together. We moved into the spoon position, with Tom behind. His cock was still pretty hard, and he positioned it between my legs so that it was touching my balls. We went to sleep in a few minutes in perfect contentment.
Morning came early the next day. Tom woke before dawn, and he got me up to witness the first light across the ocean. It was a magnificent sight, but it lacked the color of the sunset of the night before. Tom made coffee, and we sat together watching the sun come up. Tom was behind me, and I sat up close, with my butt in the V formed by his legs. Tom got hard and started rubbing his cock on my back. That made me hard, and he reached around and took my cock in his hand to jerk me off. We came in a few minutes in great spurts of jizz.
"You make me so horny," he said. "All I want to do is touch you and make you come."
"We've got to be careful of Jay," I said. "At least until he's doing it with us."
"You're right. Maybe he'll loosen up today."
We cleaned up our cum and got ready for the possibility that Jay would join us any minute. Our cocks hadn't fully subsided, but there was nothing we could do about that. We were both determined to remain naked as long as we could, and Jay would just have to deal with what was going on.
Jay came on deck a few minutes later looking a little sleepy still. He had finally taken off his shirt, so he was wearing only a pair of shorts and sandals. Tom and I put our sandals on against the coming heat of the day, and Tom fixed breakfast for us. Jay kept looking at our cocks, no doubt wondering why they were distended and shiney. He had a nice bulge in his shorts, and already the pre-cum was starting to leak through his underwear.
"How'd you sleep, buddy," I asked Jay.
"Great. I felt like a baby being rocked by its mother. That was the first night I'd slept on a boat, and it was neat."
After breakfast, we decided to go on the island to explore a little. I had a fanny pack that held a pack of cigarettes, my lighter, my camera, and the keys to the boat. I also took a bottle of sunscreen in case Jay needed it. We had a small dingy to get us over to the island, so we loaded up.
We walked along the beach for a way and found a nice place to stop. There was a small river that ran out into the ocean, and Tom decided to see where it went. Jay and I stayed put. I stretched out on the sand and took the sun. I arranged my cock on my stomach so the underside could get some sun, and Jay lay down next to me.
I propped myself up on my elbows and looked at him.
"You don't have much of a tan. I've got some sunscreen. You really ought to put some on so you won't burn."
"I guess you're right," he said.
"Here, I'll do it for you." I squirted some sunscreen in my left hand, rubbed my hands together, and started on his face and neck. At first Jay was a little tense at being touched, but he relaxed pretty quickly. I covered his shoulders and back, and then I turned him around to put some on his chest and stomach. I purposely rubbed some into both nipples, and Jay kind of gasped when I touched them.
"What's the matter," I asked.
"Nothing. That just felt kind of, er, unusual."
I took both of them between my thumb and index finger and gently pinched them. He gasped again.
"Do you like that," I asked.
"Er, well, er, yeah. Kinda." He adjusted his crotch, and I was sure his hard-on was getting uncomfortable in his shorts and briefs.
I continued down his chest and stomach. Then I made him stand up so I could put sunscreen on his legs. His shorts were pretty baggy, and I reached my hand all the way up to his crotch. I "accidentally" touched his cock, but he didn't flinch. He was breathing kind of hard by this point.
When I saw he didn't object to what I had done, I said, "Why don't you take your shorts off. You can get a better tan, plus it feels great to be naked and free in nature."
"No." That was all he said, so I didn't press the matter. After I was finished, we lay back down.
"I don't like to be naked around other people," he said, without prompting.
"Why not? It's perfectly natural, and what better place than here to be natural?"
"I know it's natural, but I guess I'm a little self-conscious. I'm always afraid something will happen."
"You mean like getting a hard-on? That's natural, too, man. I get 'em all the time. So does Tom. Every guy does."
"Isn't it embarrassing? I mean, this morning, when I came on deck, you and Tom both had partial erections. Weren't you embarrassed?"
"But, see, you got hard when you saw us. You couldn't hide it, and we both noticed." He blushed a little. "In fact, you're hard right now. And you're putting out pre-cum that's making a wet spot on your shorts." He looked down to confirm what I had said, and he blushed more deeply.
I continued: "Do you ever jerk off?"
He nodded slightly.
"Well, so do I, and so does Tom. Have you ever jerked off with another guy?"
"No," he said softly.
"But you've thought about it, haven't you? You've wanted to, haven't you? You'd like to do it right now with me, but you're afraid, aren't you?"
"Let's change the subject," he said.
"Only if you'll let me know when you're ready to do it, okay?"
He didn't say anything. The conversation had gotten me pretty worked up, and my cock stood away from my body at a forty-five degree angle, even when I lay down. A large drop of pre-cum had formed at the slit, and it dropped down onto my stomach, leaving a thin hair of the stuff connected to my cock. Jay looked at it, and it must have made him even more aroused than he was.
"You can touch my cock, if you want to," I said. He didn't do anything for a few minutes, and then a tentative hand moved toward me. Gently, almost imperceptibly, he took the shaft into his fist. He didn't move his hand, though.
"Stroke it," I whispered. "Make me come."
I could tell he found this difficult but couldn't resist. He started moving his fist up and down very, very cautiously and gently.
"Use the pre-cum to lube your hand," I said.
He put his palm over the top of my cock and got some of the natural lube I was putting out. Then he went back to stroking. His hand passed along my cock with much less friction, and it was really starting to feel good. "Do it a little harder and a little faster," I said. He complied with my request. In a few minutes, I tightened my groin muscles to make myself come, and I spurted semen all over my stomach. Some of it got onto his hand, and he looked like he didn't know what to do with it. "Rub it on my chest," I said. "It'll dry in a few minutes." He did that.
I didn't waste any time because I didn't want him to start getting second thoughts about what was going on. I lay him back and undid the button on his shorts. "Just relax and enjoy this," I said. I gently pulled his shorts and briefs down to his thighs, and I started jerking him off. He was so aroused it only took a few strokes, and he came like a fountain. I rubbed his cum into his chest. Then I got out the sunscreen and applied it to the area I had just exposed. He was very white, and he would need a lot. After I had put it all over his upper thigh and lower stomach, I took his cock into my hand again and started rubbing the sunscreen all over it. Like me, he was still very hard, and he came a second time in a matter of minutes.
When he had calmed down, I asked, "Did you like that?"
He didn't respond.
"I liked it when you made me come," I said. "I liked it a lot. It's okay if you liked it, man. You were supposed to."
"This is so new to me. You were right when you said I had thought about it. In fact, I think about it all the time. I was really hoping you'd do something, and you did. Thank you."
"You're welcome. And thank you, too." After a brief pause: "So, you did like it." "Yeah, Nick. I did like it." In a moment, he asked me, "You and Tom do that, don't you?"
"Yes. And other things."
"I heard you guys last night. I wanted to be out there with you, to watch and to, er, do it, too. Do you think Tom would do it with me?"
"I'm pretty sure he would," I said. "I'm sorry we disturbed you last night. We tried to wait until we thought you were asleep. We didn't mean for you to hear us."
"I know. Do you think it's wrong? You know, what we just did?"
"No, I don't. There are people who do think it's wrong, but I'm not one of them. And neither are the people I know. My friends."
I wanted a cigarette, so I got up and got my pouch. I lit up, put the pack and lighter back, and came back to where Jay was.
"You said you and Tom do other things. Like what?"
"Things you've probably thought about doing, too. Like blow jobs."
"And what else?"
"What do you think?"
"Do you, like, er, you know, do you . . . ?"
"Do we fuck each other? Yes. We fuck each other."
His cock was getting hard as he asked that question. The next logical move would have been for me to give him a blow job, but I didn't relish a cock full of sunscreen in my mouth. Jay was sitting up with his legs folded Indian style. I gently pushed him onto his back, and I got on top of him. I kissed him, and he responded with surprising heat. Then I sat up and worked his nipples with my fingers. They got hard in no time.
"Do you like the way that feels," I asked.
"Yeah. I've never felt anything like that before. I didn't know my nipples were so sensitive."
I kept working them, and he moaned with pleasure. I next moved my ass back toward his cock. I got up on my knees, took his cock in my right hand behind my back, and put it at my asshole. I gently lowered myself onto it. The look on his face was incredible. At first it was surprise, and then it was intense pleasure. I continued moving down on it until he was inside me all the way. I grinned at him.
"How do you like that? Do you like the way it feels?"
"God, yes. It feels incredible. It feels like we're one person."
"Good. Now I'm going to move up and down on it to make you come and to stimulate my insides. There's a gland called the prostate. . . ."
"I know. I've read everything about this I could get my hands on."
"You don't have to just lie there. You can thrust up into me, too. Try to thrust up when I'm coming down, and vice versa. Okay?"
"I'll try."
It was awkward at first, but pretty soon we got a rhythm of sorts going. I leaned over and kissed him, giving him my tongue, and he kissed back. Then I said, "Fuck me, you stud. Shove that hot cock in my ass. Make me come." That was all it took. He stiffened under me, and, in a second, he blasted his cum into my guts. I concentrated hard on feeling his spurts, and I felt his cock bounce inside me. I stopped moving and let him catch his breath. There was no way he would be getting soft any time soon, and I kind of wanted to come, myself.
I jerked my cock to keep it hard. I liked the feel of his six-and-a-half inches in my butt, so I kept still for a few minutes, biding my time.
"Now I want to come," I said. "When I do come, my ass is going to contract, and it'll push you out if we're not careful. I'll try to tell you when it's going to happen. You lunge into me as far as you can go. If we're lucky, you'll come again the same time I do."
I started moving up and down again, and it took another ten minutes for me to get off.
"I'm coming," I said. Jay did as he had been instructed. I pushed down on him as far as I could, and he plunged up into me all the way. I came hard, and that set Jay off. In a second we were both bucking against one another, dumping our loads.
When we separated, we were both covered in sweat and cum. I had no idea of the time, but it was still before noon. Already I had made it with two guys.
"You need some sunscreen on your butt," I said, "and you could probably use more on your cock." I got the sunscreen out and liberally splashed it on his ass. I rubbed it pretty well, and I even snuck a feel of his asshole. He kind of clinched when I did that, so I decided to wait until later to pursue his butt. I put another generous portion on his cock, and--surprise, surprise--he came again as I stroked it in.
"You're a fuckin' horn-dog stud, man," I said, grinning. He grinned back.
"I've waited a long time to meet you," he said. "I've got a lot stored up."
We lay in the sun for a while, then Tom came back from his explorations. I winked to let him know everything was cool with Jay. He didn't say anything about his nakedness, and he didn't even let on he noticed.
"You guys have to see what I found. It's a fucking waterfall. It's terrific. There are a bunch of rocks all around it that have been worn smooth by the water. It's better than a water slide."
"Let's go. I'm ready," I said.
"Why don't we get something to eat first," Tom said. "It must be near noon. But whatever time it is, I'm hungry."
"Cool," I said. "Let's go back to the boat and get whatever there is for lunch. Jay, wait here for us."
Tom and I took off in the dingy for the boat. I knew he wanted to talk about Jay and what had happened in his absence.
"So, what did you guys talk about," Tom asked, as soon as we were in the boat.
"Sex," I said.
"Did you bring it up, or did he?"
"He did," I said. "At least verbally."
"What the hell does that mean--verbally?"
"Well, I put sunscreen on him, and I tweeked his nipples and touched his cock through his briefs when I put my hand up into leg opening of his shorts. Then I told him to take off his shorts. Then he brought it up."
"What did he say?"
"He was embarrassed to take off his shorts because he was afraid of getting a hard-on. He had one, of course, and I told him we both knew he did. He asked me what the two of us did, and I told him. Then he said he wanted to watch us last night, or, er, do it with us. Then he asked me if I thought you would do it with him, and I said I thought you would."
"Go on. Don't stop now."
"Then I got a hard-on, and he jerked me off. Then I took off his shorts and jerked him off. Then I put sunscreen on his cock and jerked him off again. Then I got on top of him, and he fucked me. Nothing much."
Tom laughed at that last statement. "Jesus Christ, you took his fuckin' cherry. My hat's off to you."
"Yeah," I said, and I laughed, too.
After a short silence, I asked, "Tom, are you really hot for this kid, or what?"
"No, dude, but I am really hot for you. I just thought that it would be a whole lot easier for us and for him if he was part of what we were doing. I'll fuck him if he wants me to, but you're the only meat I'm interested in. He'll probably be after your ass, too, so you better watch out. Like I told you, you're going to be fucking your ass off on this trip."
"You know, I don't seem to mind that idea."
Tom laughed. When we got to the boat, I went to the galley to get some lunch for us to take back to the island, and Tom went to check on the noise that was coming from the radio. I heard him place a call, but I couldn't hear what he was saying. It took him a few minutes to do whatever he was doing.
When he came back, he had a big grin on his face.
"What's up," I asked.
"I had a radio message from the guy whose place you're taking. He said he was able to clear up the little problem that kept him from coming, and he wanted to know if he could fly out and join us."
"What did you tell him?"
"I said hell, yes. This'll be great, see. With four of us, we can pair off. We won't have to worry about Jay being the third man out. Not only that, I talk a good game, but I feel a little funny about fucking my own son. Even if I don't know him."
"I thought you did," I said. "When's the guy getting here?"
"This afternoon. He was calling from Key West, and he said he could get a plane out in an hour. I gave the pilot our coordinates, and he knew right where we are. They'll fly in on a seaplane. In fact, I think I'll wait on board to make sure I'm here when he arrives."
"Who is this guy?"
"His name is Terry Garcia, and he's maybe twenty-six or twenty-seven. I told you I like younger men."
"I don't know him," I said.
"He's a nice guy. Real good looking, and pretty well put together. I've known him about a year."
"Is he going to like Jay? And is Jay going to like him?"
"I hope so, to both questions. We'll just have to wait and see. For now, you go back to the island and keep Jay company. Y'all really ought to explore the falls. They're pretty cool."
I got back in the dingy with the lunch stuff. I burned my ass when I sat on the hot seat, but it cooled off pretty quickly. Jay was stretched out in the sun when I got back to the island.
"Where's Tom," he asked, as soon as I had landed.
I told him about Terry and that Tom was waiting for him.
"I guess I'll be the only kid, then. Oh, well, it'll be fun."
We ate lunch, and the whole time I was thinking about his last statement. I wondered how old he thought I was. I decided to ask.
"How old are you, Jay?"
"Eighteen. I just had a birthday two weeks ago."
"So, you'll be going to college, right?"
"Yeah."
"Where?"
"Yeah. I plan on it. Florida State. Maybe the University of Florida, though. I'm not really sure."
"How old do you think I am," I asked.
"I don't know. Twenty-four, twenty-five."
He didn't seem interested in pursuing the subject, so I let it drop. After we had finished eating, I smoked a cigarette, and we kind of cleaned up the sandwich bags and stuff. I had brought four cokes, two for lunch and two for later. I knew Tom didn't want us back on board too quickly.
"Let's go find the waterfall," I said, and we took off.
The fall was as nice as Tom had said it was. We stood under it, feeling the heavy crash of the cold water as it came off the cliff. We played on the rocks and slid down them. We did a double slide. Jay got behind me with his legs entwined in mine, and we slid down together. Being that close to me gave him a hard-on, but I didn't do anything about it. I wanted him to get used to walking around hard without being embarrassed.
We swam in the pool the fall made, and had a good time ducking and wrestling with each other. I felt his hard-on brush me in several places as we fooled around. After a while, I got up onto a relatively flat rock to rest. Jay got up next to me. I lay down to rest, and he put his hand on my chest. He started working one of my nipples, and that made me hard.
"I like it better when we both have erections," he said.
"Me, too." Pause. "Jay," I said, "why did you say 'erections' instead of hard-ons?"
"I'm not used to talking like that, I guess. You and Tom use all the slang words, and I like that. In fact, it kind of turns me on. But I just feel uncomfortable saying them."
"You gotta get over that, man. You gotta call a hard-on a hard-on. You've got to say 'Nick, I want to fuck you.'"
"You want me to say it now?"
"If you want to," I said.
"Okay. Nick, I want to fuck you."
"See, that wasn't hard, was it?"
"No, not really. But my cock is, and I really do want to fuck you." We both laughed.
"You gotta kiss me before you can fuck me," I said.
He didn't waste any time. He leaned toward me and kissed me hard. He slipped his tongue into my mouth on the first pass, and we lay on our sides, kissing and tonguing. We were both breathing pretty hard.
"You know what I want," I asked.
"What?"
"I want us to rub our cocks together. Here. Let me show you." I moved a little closer to him and shifted him more onto his side. Our cocks were standing out between us, and I moved around so that mine was touching his. He started moving, too.
"That feels good, doesn't it," I said.
"Yeah, dude, it does. I think you could make me, er, come like this."
"Don't hold back. If the urge hits you, then come." I wanted him to fuck me, but I wanted it to last. I figured if he came before he entered me, I'd have a better chance of a good ride. I didn't have long to wait. He blasted forth in just a few minutes. I rubbed his come all over his cock, and I got on my back.
"Your cum will be a good lube," I said. "I'm going to put my legs up on your shoulders, and I want you to bury your cock in my ass. You ready?"
Instead of answering, he got into position and drove his rod home. It wasn't too big and it wasn't too small. In fact, it was the perfect size.
"Push back on my legs as you fuck me," I said. He did as I said, and the head and top side of my cock rubbed on my belly. If he could hold out long enough, that would be enough stimulation to make me come. We got a good rhythm going pretty quickly. Apparently, this boy was a fast learner.
I always liked this position because it let me see the other guy's face. Jay's face was a masterpiece of expression. Every time he plunged in or pulled out, the pleasure he felt registered on his face. When he finally came, he made a face that said "ecstasy." I came with him, and it was long and hard and intense.
I got a cigarette from my pouch and crawled back onto the rock next to Jay.
"How was it this time," I asked.
"Better than the first time," he said. "I wasn't as nervous, and I knew better what to do."
"You're getting better at it. We're just going to have to practice, that's all." He laughed.
After a short pause: "What does it feel like?"
"What does what feel like?"
"Having my cock in your ass. Does it feel as good as they say it does?"
"Yeah. It feels good. It feels real good. It's hard to say what it feels like, though."
"Well, try."
I thought for a moment. "You know how it feels when you have to take a shit real bad, and a fat turd slides out of you? Do you like the way that feels?"
He thought for a moment, too. "Yeah. I never really thought of it, but that really does feel good."
"Well, that's sort of the way it feels. Only the turd never goes out. In fact, the other guy keeps plunging in and out, over and over."
"What does it feel like when the other guy stimulates your prostate?"
I thought some more. "That's impossible to describe," I said. Then, "Do you ever stick your finger up your ass when you jerk off? Your finger or anything else?"
"No. Never have."
"Do you want to try it? I'll do it. Use my finger, I mean."
"Does it hurt?"
"Does it hurt when you shit?"
He thought about it. "No, but shit's soft."
"So is my finger. So is my cock, for that matter. Hard and soft at the same time."
"I guess we can try it."
I got the sunscreen out of my pouch and lubed my finger up really well. I put him on his back and had him open and lift his legs. I played with his asshole for several minutes, then I slowly stuck my finger in. I arched it up to where I knew his prostate was, and I started massaging it.
"How does that feel," I asked.
"Incredible. Really incredible."
"Okay, now jerk yourself off."
"You do it," he said. This guy learns fast, I thought.
I reached for his cock and started stroking. It didn't take long. In a minute, his asshole contracted hard around my finger. I shoved it in as far as I could, and he started spewing cum.
"How was that," I asked.
"That was the most intense orgasm of my life," he said, still a little breathless.
"Well, it's like that, only better, with a cock."
He lay back quietly, and I could tell he was thinking about having me fuck him. He wanted it, but, like everything else about sex, he was a little scared.
In a few minutes: "Your cock is so big. Are you sure it won't hurt?"
"I'm going to level with you. It will hurt a little, at first. There's a ring of muscles that keeps your shit in, and yours in pretty tight because it's never been stretched. You can relax it, but that takes a little practice. The first time, it'll probably hurt when I shove my cock head past the ring. Once that's done, though, the rest slides in pretty smoothly. One thing you can do to make it easier is to press down like you're taking a shit. That'll make the muscle open up some. Also, I'll fix it so you're in control."
"What do you mean?"
"I'll let you get on top, and you can take it as slow as you want. But, hey, listen. I want to fuck you, but only if it's cool with you. I ain't into rape. Any time you say 'stop,' I'll stop. And we don't gotta do it now. Or ever. Okay? Sex is supposed to be fun, and if it ain't, fuck it."
He seemed to relax when I said that. His cock was rock hard, and I knew he wanted it. I jerked mine a few times to get it hard, just in case he was ready.
When he saw me do that, he crawled over to me, gently shoved me down, and straddled my groin. "Let me lube up," I said. I covered my cock with a generous amount of sunscreen. "Okay."
He slowly moved down onto my rod. I positioned it at his asshole, and the first little bit went in without a hitch. Then it hit the sphincter ring.
"Make like you're takin' a shit," I said.
He did as I told him, and part of the head opened the ring.
"Take it slow," I said. "We ain't gotta rush this. Let your muscle ring get used to having this big turd into it."
I could feel the tightness of the ring relax a little, and he pushed down a little more.
"I'm almost in," I said.
He waited another few seconds and pushed again. This time the head made it past the ring. He grimaced a little, but his face didn't show real pain. In a few seconds, he pushed more, and this time my whole shaft slide into him. His balls were nestled in my bush, and his cock stood up straight in front of him.
"Okay," I said. "I'm in. Start moving up and down whenever you're ready."
He waited another few seconds and started pumping. He was real slow and cautious at first, and he didn't move more than an inch up or down.
"Can you feel it on your prostate," I asked.
"Not really. It feels good, but it's not like it was with your finger."
"Lean back a little. You're bent forward too much."
When he sat up straight, the feeling inside him registered on his face.
"That's better, isn't it?"
"Oh, yeah. That's it, man. That's fabulous."
"Okay, now pump. I won't thrust just yet."
He started pumping slowly, but in a few seconds he picked up speed. Without saying anything, I started thrusting, and the pleasure washed over his face in wave after wave. After ten or fifteen good, long pumps, I grabbed his cock and started jerking it. He started moaning pretty loud, and I knew he was close. He screamed "Yeeeesss" when he came. I came a moment later. He made a big puddle of cum on my stomach and chest, and he slumped over into it when he was finished. We stayed like that, with him on top of me, for several moments, and finally my cock was too soft to stay in.
"Jesus," he said, when I was out, "I didn't know what I was missing. I think I'm in love with you, Nick."
I laughed. "Don't say that, man. It's bad luck. I probably won't be able to get it up next time." He laughed at that.
As I was lighting a cigarette, the seaplane carrying Terry circled and landed. We couldn't see it, or even hear it very well, but we both knew it was there. Jay started getting a little nervous.
I put my hand on his chest and rubbed it a little. "Hey, man, don't get nervous. You don't have anything to be ashamed of, and this guy will probably want to fuck the shit of you as soon as he sees you."
He laughed. "You're a kind person, Nick. You know that?"
I kind of shrugged. I finished my cigarette, and then I suggested we get in the water to wash the cum off ourselves. In about thirty minutes, we had picked everything up and were getting into the dingy. The ride back took five minutes. We tied up and went aboard.
Tom and Terry were waiting for us on deck when we pulled up in the dingy. Tom was in his birthday suit, just as he had been earlier, but Terry was dressed in khaki shorts, a long-sleeve blue pinpoint oxford shirt with the sleeves rolled up, and high-top hiking boots with white socks about the tops. He was the picture of "prep." He was also the picture of gorgeous. He was probably six feet, maybe 175 lbs. He had black hair that was a little long and perfect bright-white teeth. If he wasn't a model, he should have been one.
Jay and I straggled on board, carrying our stuff. Tom came over to give us a hand up the ladder, and we dropped our stuff where we stood.
"Terry, this is Jay Calderon and Nick Marshall." We both shook hands with him, and he looked us over, up and down.
"Hi, Terry," I said. "Glad you could make it today. But not yesterday. I wouldn't be here if you had." They all laughed.
"Glad you could make it, Nick. I would have been up shit creek if you hadn't been able to come along. I guess we owe each other."
"Jay and I have been exploring the falls, Tom. They're fantastic. I don't think I've ever seen anything like that. You were right; they're much better than a water slide." Again, laughter.
I could tell this guy really liked my looks. Hell, we weren't all that different in appearance. We were almost exactly the same size, but I had more muscle than he did. He glanced at my cock several times, and I wondered how he compared.
"Aren't they great," Tom said. "They might be worth another trip over. What do you say, Nick?"
"I say, this Noo Awlins boy needs his afternoon cup of coffee first. We can talk about adventure after the caffein level gets back to normal." Again, laughter.
Tom went to make coffee, and the rest of us sat in deck chairs.
"Where do you live, Terry," I asked.
"Tampa. You ever been there?"
"No," I said. "Maybe soon, though."
"I have," Jay said. "I love Ybor City. I guess you know it."
"Yeah, I know it. Very well, in fact. My dad owns a cigar factory down there, and I used to work in it when I was in high school."
"You know how to make cigars," I asked.
"Well, I could probably do okay with one. My job was to read to the workers, though."
"Like Samuel Gompers," I asked.
"That's right! Wow! Not many people know who he was, anymore."
Tom came out then with coffee. I took a cup, and so did Terry and Tom. Jay passed. I dug in my pouch for my pack of smokes and fired one up.
"You mind if I have one of these," Terry asked.
"Of course not. Help yourself," I said. Tom took one and lit up, too.
"I thought you would be a cigar smoker," I said to Terry.
"I smoke 'em occasionally, but I'm a cigarette addict. Cigars are too, I don't know, old-manish for me. They're okay after a big meal or something, but cigarettes are my regular fare. And, by the way, I do have several cartons, so I won't be bumming yours the whole trip." He grinned when he said that, and his look was perfect.
I was starting to like this guy. He seemed pretty smart, and he obviously liked looking at me. I slouched back in my chair and opened my legs. This made my dick hang over the edge. Tom and Jay each put on about an inch of dick when they saw that, and I figured Terry must have done the same.
When we finished our coffee, I suggested we go back to the island and explore the falls. Before we could get ready to go, a school of dolphins came up alongside the boat. Tom noticed them first.
"I think I'd rather swim with these guys," he said.
"Oh, wow! I would, too," I said.
Tom led us down the ladder into the water with the dolphins. I was second, Jay was third, and Terry, who apparently had taken off his clothes while we were on the way down, was fourth.
The dolphins were great. We rode on their backs, held on to their undersides, and played tag with them. There were six of them, apparently parents and four children. The parents were gentler than the kids, and they pushed us under and lifted us up time and again. We probably stayed in the water with them two hours, and they seemed to understand we were tired when we dragged ourselves up the ladder to get out.
When we were back on deck, Tom went to the galley and got a large bag of something and dumped it into the water. It was an assortment of frozen fish, and the dolphins went crazy eating it. As it turned out, that was probably the best thing Tom could have done because those dolphins stayed with us throughout the rest of our cruise of the Caribbean.
After we got out of the water, I asked about taking a shower. I had been wet several times that day, but the last time was in salt water, and I really wanted to wash it off. The others agreed that a shower was a good idea. Tom said the supply of fresh water on board was obviously limited but that we could save water if we showered together. Basically, there was a shower head connected to cold water. We could get wet, soap up, and then rinse off. That would save the most water.
Tom brought out a bottle of shampoo, two bars of soap, and four towels. We all got wet, and Terry said he thought we should wash each other. That was fine with me. Terry grabbed the shampoo, poured some into his hand, and started lathering up my hair. I did the same to him, and pretty soon Tom and Jay were washing each other's hair, as well. We rinsed our hair, and then we started on each other with the soap. Each pair of guys had a bar, so we had to swap it back and forth. Terry started on my face and then moved down to my chest. He was concentrating on my nipples, of course, and before long the inevitable happened: I sprung a boner. I did the same to him, and he got hard, too. Tom was washing Jay, and Jay's cock was as hard as it had been all day. I was a little worried that Tom might be having strange feelings about the whole thing, but his cock was just as hard as everybody else's.
In a few moments, Terry and I were covered in lather. He pulled me to him and put an arm around me to "wash" my ass. I pressed up against his chest, and our cocks touched one another. That send an electric charge through me. This guy was a real hunk, and his seven-inch uncut cock was really turning my ass on. When he had finished with my ass, he pulled me to the deck. Tom saw what we were doing, and he and Jay got down with us. I took that opportunity to pull away from Terry and turn my "washing" attention to Tom. That seemed to be okay with the others, too, and Terry and Jay looked like they were having fun getting clean. I moved Tom onto his back.
"I think your ass needs some deep cleaning," I said.
"I think you're right," he agreed.
I pushed his legs back and entered his ass. It felt really good to be in him and on top of him all covered with soap. We slid around, and the friction was smooth and wonderful. Terry was on his back, and Jay was "washing" his ass, just as I was Tom's. Jay came first of all of us, and Tom and I were next, on cue. Terry was jerking his own meat, and he came in a loud groan. Once I was out of Tom, Terry grabbed me before I could protest or do anything to prevent it. He got me on my back and plunged into me without a word.
Tom and Jay watched for a few seconds, then Jay said, "Come on, Tom. What are you waiting for?"
Tom didn't flinch or say anything. He got Jay on his hands and knees and entered him from the back. This time Jay did the moaning, and all four of us came a second time in just a few minutes.
As we were lying on the deck, recovering, Tom got a hose and squirted us all clean. Terry pulled back his foreskin all the way to wash out the soap and jizz and whatever else was under it, and I watched shamelessly as the bright reddish-purple of his cock head took the streaming water.
Once we were clean and dry, Tom asked me to go with him to the galley to make drinks while he started dinner.
"Thanks for trying to spare me," he said. "But I figured it had to happen, and this was as good a time as any. Jay's pretty hot. You're a good teacher."
"Thanks," I said. "I'm glad it wasn't too painful for you. Did you have any qualms of conscience while you were fucking him?"
"No. I thought about that a good bit after you left this afternoon, and I decided if he wanted it, I'd give it to him. There's no feeling between us."
"Good," I said. "You asked me if I had ever fucked my dad, and I said no. The only reason was I never had the chance."
Tom grinned at me and pulled my dick.
We had our drinks and watched the sunset while Tom grilled steaks. After the sun went down, we watched a video of a movie with Lorenzo Lamas that I had already seen. Halfway through I got real sleepy and went to sleep for the night. It had been an early day and a busy day, and I was tired. At some point, I half awoke when I realized somebody was carrying me in his arms. It must have been Tom. The next morning I woke up in bed with Jay.
When I awoke, Jay was already awake next to me. The bed was supposed to be a double, but it was narrow, so he and I were touching. I stretched and luxuriated in the comfort of his warmth and the gentleness of his body next to mine.
"Hi," I said.
"Hi, cutie," he said, and he gently kissed me on my lips. That was a first for him, and I figured it meant he was getting a little confidence in himself.
"What time is it," I asked.
"It's around seven."
"The other guys must still be asleep. I don't hear anything."
I had a very hard boner because I had to take a piss in the worst way. I pulled the sheet back to see if Jay was hard, and he was.
"I gotta piss," I said. "Come on."
We got out of bed and went into the little hall that separated the cabins. There was a bathroom, or head, at the end of the hall, but I knew I'd never be able to piss into it in the condition I was in. I climbed the steps to the deck, Jay right behind me. We went over to the side of the boat and pissed into the ocean. I noticed the dingy was gone, and I found a note from Tom on the table on the deck saying that he and Terry had gone to explore the island. We were to use the fog horn to call them if we needed them.
"Do we need them," I asked Jay, grinning.
"No. I don't think we do."
"Lets get some coffee and get back in bed," I suggested.
We got coffee, and I got my cigarettes and lighter, too, and we got back in bed.
"Tell me what you thought of yesterday," I said.
Jay thought for a minute. "I've been thinking about that since I woke up. It's hard to know what to think. I'd never done anything sexual with anybody, boy or girl, until yesterday. I'd thought about it a lot, and I had read all the porno I could get my hands on. I used to spend hours downloading pictures of naked men, and women, too, on my computer, and I used to imagine what it must feel like to be doing what they were doing. When I saw you at the airport in Key West Monday, I started getting excited. You are really a sexy guy, you know that?"
"Thanks," I said. He wasn't the first person to have told me that, but I always took it with a grain of salt. Horniness can't be trusted to tell the truth.
"I don't know what it is about you. You're beautiful. Your face is, I mean. And your body is perfect. Even the tattoo. And the way you smoke. Everything about you screams MALENESS! When you took your clothes off and I saw your cock, I almost came on myself. Anyway, as soon as I saw you I got the idea that I wanted to do something with you. Have sex. Fuck."
"You liked it, then?"
"I loved it. I was nervous, but you put me at ease. And you didn't belittle me because I was a virgin. You knew that I was, didn't you?"
"I had a pretty good idea."
Jay reached over and picked up my cock. He didn't rub it, exactly. He sort of fondled it. "I can't believe the size of this thing. You're as big as some of the bigger guys in the porno pictures."
"What you're doing to it feels good, man. Don't stop."
I picked up his cock, and he was almost hard. I moved myself down farther in the bed and took his cock into my mouth. I wanted his first blow job to be truly memorable, so I used all the skill I had. I ran my tongue around the rim of the head, and then I tongued the head. I went down on his cock all the way, but I didn't keep it in my mouth too long. I tickled his balls with my left hand, and I reached up for his nipple with my right. I worked my tongue up and down the shaft of his cock, and he moaned when I ran it along the sensitive ridge on the underside. Then I tongued his ball sack until it was tight and shrivelled against the base of his cock. I moved lower and licked the spot between his balls and his asshole, and he really moaned when I did that. I debated whether I should work his asshole with my tongue, but I decided to save that for another time.
Instead, I took his shaft into my mouth and started moving up and down on it. I used my tongue to make the space in my mouth as tight as a pussy, and I tickled his piss slit with the tip every time I pulled up on it. I could tell he was really close to exploding. I went back to the nipple-ball sack routine, and, when I did, he made a kind of loud noise that said he was coming. And come he did. I counted eight hard contractions, and he put out a larger than usual load of cum.
His cock didn't soften any after he came, so I kept it in my mouth. My own cock was really hard, and I wanted to come, too. I didn't want to distract Jay with having to get me off, though, so I started jerking myself off. He didn't really notice what I was doing, and that was fine. I sucked his cock for about ten minutes, running it in and out of my mouth and working my tongue over the sensitive places. When he came the second time, he came harder than he had ever come for me before, and his cry was pure orgasmic pleasure. I came right after him, and I spurted my spunk onto his leg.
His second climax made him soften up a little, but only a little. I could have probably pumped him hard again in no time, but I needed a break. I scooped most of my cum from his leg with my finger and popped it into my mouth. I got what I had missed the first time and offered it to him. He took my finger into his mouth and sucked it dry.
I moved back up the bed and got next to him again. I lit a cigarette.
"I'd like another cup of coffee," I said. "You want one?"
"Yeah, but let me get it." I told him how much sugar and cream to put in mine, and he came back with the two cups, plus some frozen sausage biscuits he had warmed up in the microwave. We ate breakfast in bed.
We stayed in bed for another couple of hours, rubbing, caressing, fondling each other. We stayed half hard the whole time, but we didn't really "have sex" again. Jay liked his blow jobs better than anything else so far, and he asked me if he could give me one. I told him he certainly could later, but I wanted this to be a special time for him. Sometimes I enjoy the kind of tenderness and closeness we had that morning more than sex itself. We finally got up when we heard the motor on the dingy approaching the boat.
"Hey," I called out when they killed the motor. Tom and Terry came up the ladder to the deck.
"What have you guys been up to," Terry asked.
"Nothing you haven't been up to," I said. He laughed.
"I hope so," he said.
Tom put his hand on my cock and squeezed it lightly. "Is this thing coming or going," he asked.
"Both," I said.
They told us about going back to the waterfall and playing around there for a while. We decided we'd spent as much time as we wanted to at this spot, so, after lunch of hotdogs and chili, we set sail. We made it through the Windward Passage into the Caribbean, and we set anchor northeast of Jamaica. Our family of dolphins followed us, and we decided to get in the water and give them some personal attention when we anchored. They acted genuinely glad to have us in the water with them. They're such smart animals, you'd think they were almost human.
After we showered and "washed" each other's asses as we had done the day before, we ate a leisurely dinner on deck. Terry was the chef, and he served some wonderful black beans and yellow rice, with big, hot sausages on the side. After dinner Tom gave Jay his first scuba lesson on deck, and Terry and I cleaned up the galley.
"Tom told me about Jay, and he told me about you, too. You're really quite incredible. When I was eighteen, I could barely jerk off."
"I doubt that," I said, modestly.
"No, it's true. I didn't get laid until I was twenty. And then I was so drunk I wasn't sure what was happening."
"I guess when you like sex as much as I do, you just naturally get good at it."
Terry put his arm around me and turned me to face him. He bent my head over slightly and planted a deep, wet kiss on me. I responded with plenty of tongue, and before long we were both hard as rocks and breathing hard. I dropped down in front of him and gave him a blow job that rivaled the one I had given Jay that morning. I always feel you have to make a good first impression, and that's what I set out to do. After Terry came in a body-wracking orgasm, he reciprocated on me. I came hard, too.
We went back on deck, and we talked about what we should do the next day. Terry suggested we all go onto the island and take in the city of Kingston. Tom and Jay were both eager to dive, so we compromised: we would dive and fish tomorrow, and the next day we'd go into Kingston. Tom called ahead and made a reservation at a Marriott hotel in Kingston. He figured we'd all be too drunk and too tired to try to navigate back to the boat after a day and night on the town.
Tom asked me to get my guitar, and I sang Jimmy Buffett songs for a couple of hours. I knew almost all of them, and the other guys were able to sing along on some of them. It was a lot of fun. We were drinking beer, and at eleven o'clock, we were all tired and ready for bed. I put in with Terry that night at his request. We didn't do anything that night, but the next morning we woke up early and fucked each other silly. It was a great way to start the day.
The next day, Tom and Jay dove, while Terry and I fished. The day after that we went into Kingston and did the city. We separated in the afternoon. Jay and I went down to the pool, and Tom and Terry took naps. Jay and I got lucky pretty quickly, and two girls from Argentina asked us back to their room. Our Spanish really paid off, and I think I learned some words that aren't on the school vocabulary list. Jay's sexual initiation was complete. When I asked him how he liked having sex with a girl, he just grinned.
The rest of the trip was a real idyll. We sailed from island to island, sometimes doing tourist things, if the island had any to do, but usually just enjoying the leisurely pace we set for ourselves. All four of us got to be best friends, and it was sad to tell everybody goodbye when we returned to Key West. Tom and I flew home to New Orleans on a commercial airline, and he left a few days later for the Orient. Terry went back to Tampa and then to work for his father. All in all, that summer was a great adventure.
Jay and I stayed in touch by e-mail on a fairly regular basis. He decided on Florida State University, instead of the University of Florida, and he was happy and doing very well in school. In the fall of 1999, Florida State dominated Division One football. They were ranked Number One in the pre-season, and they held that rank throughout the fall. By January of 2000, they were still Number One and were ready to play Virginia Tech in the Sugar Bowl in New Orleans for the National Championship. My brothers and I had had season tickets to the Saints that we had inherited from our parents and uncle, so we were a sure thing for Sugar Bowl tickets, if we wanted them.
I got a call from Jay the day after Christmas.
After our usual "how are you" chit chat, he said, "You know about the Noles, right?"
"The who," I asked in my most naive voice.
"Fuck you, asshole," he replied.
"Oh, Jay, don't say that. You're making me hard, man. Oh, God, I can still feel your hot, hard cock up my asshole, fucking it, making it sing with divine pleasure."
He finally realized I was teasing him, and he started laughing. I laughed, too, at my own bullshit.
"Shut up," he said, laughter still dripping out of the corners of his mouth. "I'm coming to the game, and I need a place to stay."
"Have you considered a hotel?" I couldn't control my own laughter, and he laughed harder than before.
"No, actually I haven't."
"Oh, you're staying with Tom," I said, knowing full well where this was leading and already starting to get aroused.
"He'll be in Japan," he said.
"Poor baby," I said. "I guess you'll have to sleep at one of the homeless shelters, then."
"Yeah, right."
"Oh, so when do I meet your plane?"
To be continued, maybe.