Caribbean Cruise Ch. 02: Chet Gets Laid

"But you're with another man, an older man," Chet said, the words stumbling out.

"Conrad? Yes, I'm with Conrad. But if you've seen us, you've probably correctly figured that there's not much sex going on between us anymore. But Conrad does enjoy watching me fuck other men. Have you ever done that—been watched by a third man?"

"I . . . uh . . ." Chet guessed that Julio and the Nigerian room steward had spent some time watching the other with Chet, but he hadn't paid much attention to that.

"And some light bondage. You ever allowed yourself to be completely incapacitated during sex? It gives you an incredible high."

"No. Never," Chet said, with a little gasp.

"You scared of what you and I could do together?"

"Yes . . . a little."

"But aroused and curious?"

"Yes."

"Good. Then you'll meet me in the Rose bar on board, say at 8:00 tonight?"

Chet merely nodded his acquiescence.

"Good. I'll give you a fuck you'll remember. Got to go now, though. I have other fish to fry."

The older hunk was sinking into the water to go snorkeling around the shipwreck. The forward Travis followed him into the water.

Later Chet met the other man, whose name was Doug, at the beach bar as they all were drying off from their swim. Travis seemed to have disappeared. Doug was a jeweler from New York and asked Chet a lot of questions about his life and likes and aspirations, only slowly working around to the sexual. Work around to the sexual he did, however, and the questions Doug got around to asking and the time he took getting there made Chet think that Doug's interest in him might be longer term than just a tumble in the hay. This both frightened and aroused Chet. This was the sort of hook up he'd been dreaming about when he came on this cruise. Of course his fantasies of this had the face on it of Bud, the assistant football coach, but this Doug was a lot like the coach in many ways. He was about the same age, and he was as handsome and well built as the coach was.

"I come down to Florida often, but have you ever thought of maybe living in a big city in the north, like New York, after college?" Doug asked. He already was leaning into the barstool that Chet was sitting on and had an arm draped around the back of Chet's barstool. "Or even finishing off college in New York. I'm sure they have an excellent sports management program at NYU or Colombia."

"Uh, no, I haven't thought about that," Chet said. But then he added, "But it's certainly something to think about." He was letting Doug do the leaning. He was getting a little skittish. This was so much what he had hoped to be getting into on this cruise. Much more than the exotic sex. Not that he didn't really, really like that too. He was learning so much so fast.

"Do you like young men or older men? I thought maybe older men. I've seen you with that Brazilian."

Has everyone seen me with Julio, Chet wondered, in exasperation. He tensed up a bit at the mention of Julio, and Doug sat back in his chair and withdrew a little as well.

"Sorry, I didn't mean to rush you."

"Uh, you didn't rush me. You've just given me a lot to think about. I think I like older men."

"But not as old as—"

"No, no. You're fine. You're more than fine. I like you fine."

"Maybe we could meet on board sometime then, and—"

"I'm sure that would be—"

A shrill voice, dripping with sarcasm broke in. "There you are Chet. Wondered where you'd gone off to. We have something for you over here. Come with me, dude."

Chet turned to see that his frat brother, Steve, was bearing down on him. A couple of other fraternity brothers were walking with him. They were strutting and punching each other's arms, and generally acting frisky.

"That's Steve, the frat president," Chet turned to Doug and said. "When he calls I gotta go. But . . ."

"But you'd be willing to meet me on the ship."

"I . . . I—"

"Come on, dude, let's do this thing." Steve and the frat guys hustled Chet away from the beach bar and over to the fringe of the beach some distance away and behind a couple of small fishing boats turned on their sides.

The young woman was probably a local. She was naked and voluptuous. Not much to look at in the face, but that's not what she was there for. She was backed into one of the frat boys, who also had lost his Speedo, and the two were standing close, her back to his front, with one of his arms encircling her waist and the hand of the other arm cupping one of her ample breasts. She was smiling and moaning, so it was evident she was game for this. There was little doubt the frat brother had his cock inside one of her holes.

"Time to do it, bro. Time you joined in."

Chet broke away from the two brothers who were holding his arms. "I said that I'm getting it already. I prefer older women," Chet said angrily, clutching at any reasoning he could to get out of this and remembering what Pat had said on the tender ride over from the ship about Ben Franklin's opinion on older women and sex. "I'll get your proof to get you off my back, but I'm like Pat. I don't go in for gang bangs. And I pick my own. Now just get off my back about this."

He turned and strode away before Steve could take charged and make sure he carried through. He wanted to go back and tell Doug he'd love to meet him on the ship and that he'd love to fuck him—Doug had made quite clear that he was solely a bottom. It probably was just having gotten two propositions so close together like this. Or maybe it was that Doug was hinting at a long-term relationship possibility, which is just what Chet had come on the cruise looking for. Whatever it was, Chet knew he should have said he was willing to meet Doug—was thrilled at the idea of having sex with Doug—straight out.

He felt doubly so when he got back to the beach bar, because Doug was gone.

* * * *

Chet's cheek was flat on the bedspread at the foot of the twin bed in Travis' cabin, and he was staring wildly at the lumpy old man, Conrad, sitting in a club chair only six feet away. The old man was naked, was watching Chet's eyes intently, and was pulling on his own meat.

Chet would be screaming if the ball gag in his mouth would permit him to do so, and he'd be using his arms and legs to try to scramble away from the deep thrusting of Travis' monster cock, if he could. But he was bound to the bed. His arms were pulled back along his sides and were bound at the wrist to thick straps around his thighs. His legs were bound at the ankle to restraints that traveled down to the legs of the bed at the headboard, and there was a collar around his neck with restraints pulled tight on either side and running down to the legs at the foot of the bed.

He was on his knees, with Travis crouched over his hips, fucking him hard and deep, and chanting in a raspy voice, "You love it, you love it, you love it."

And the strange thing for Chet was that Travis was right. Chet did love this. Julio had awakened in him the urge to know it all, to know everything that one man could do to another. Chet wouldn't want a steady diet of this, and this would dissuade him from any thought of an arrangement for the future with Travis. But this, right here, right now, Chet was loving. He didn't even mind that the man toad—Conrad—was watching him being bound and fucked with his eyes bugging out and his beefy hand pulling a trickle of cum out of his fat cock.

They were paying homage to Chet's body and his youth, and he was building up to one fine ejaculation.

Except that Chet was wrong. Before Travis let him go, Chet had three ejaculations. After resting from the fuck on the bed. Travis rebound Chet's wrists to his ankles and rolled him up on his shoulders on the floor, mounted him from above in reverse, and jack-hammer fucked him. The third time, with Conrad still watching and licking his chops but sitting on the bed this time, Chet was bent over the club chair, with his wrists and ankles bound to the four legs, and Travis slow-fucked him from behind. When they had both come, Travis left Chet there to watch while he went over and sank between Conrad's knees and gave the old man a long, coaxing blow job.

When Chet went down to his own cabin that night, he found himself alone. Pat was out all night, no doubt in some older woman's cabin. It gave Chet the time he needed to rethink what he wanted from this cruise and these experiences. Of them all, the man at the beach bar, Doug seemed to be the one he was most simpatico with. He was so much like the assistant football coach Chet fantasized about. And from how he was pitching Chet, it seemed he was interested in a long-term relationship. But they would have to fuck first. Chet would have to know the man could satisfy him in bed—and that he could satisfy Doug's needs.

* * * *

The next day the ship docked at Cozumel, Mexico, at 6:00 a.m. for the second of the two destination ports of the five-day cruise. In his conversation with Doug at the Grand Cayman beach bar the previous day, Doug had revealed the beach excursion he'd signed on for Cozumel. After breakfast, Chet went to the excursions desk and managed to sweet talk a young female clerk and make his way onto the same tour.

Chet saw Doug going down the stairs to Deck 2 to walk off the ship and moved to catch up with him, but the tour desk clerk delayed him, angling, he thought, for an invitation for a drink or something. By the time Doug got onto the pier and had found where the tour to the beach was gathering, people were already getting on the bus and there weren't any seats open near Doug. To Chet's surprise, Julio was on the bus as well, and there was an empty seat next to him, where Chet sat. While the bus was moving, Julio draped his towel over Chet's lap and played with Chet's cock through the tight material of the Speedo while Chet tried to act like he wasn't being aroused and panted shallowly to keep from moaning out loud.

He was sure that Doug had seen him, that he knew Chet was there, but Doug wasn't acknowledging him. Chet did almost catch up with him when they got off the bus at the beach, but Julio was pulling him aside and saying, "I don't really like this beach. I see a cab driver over there I know. He'll take us to another beach—a much more private beach."

Chet took one last look at Doug as he was being dragged toward the taxi by Julio, and Doug looked back at him. His stare was more pained than blank, but there was no doubt that he wouldn't make any offers to Chet himself.

Julio and the cab driver, introduced as Angel, did indeed seem to be close friends. Angel was middle aged but muscular, almost simian because his arms and legs seemed a bit too long for his body which, if anything, was muscle bound. He was dark skinned and had wavy black hair with some gray at the temples. As Julio talked to him, he turned hooded eyes on Chet and gave a lascivious smile and smacked his lips. Julio pressed a good deal of money in his palm as Angel looked over at Chet and inclined his head. Julio said something with a nod of his head, and the cab driver smacked his lips again, and with a smile opened the cab doors.

Julio put his arm around Chet in the backseat as the cab sped out into the countryside. He put an arm around Chet's shoulders, pulled the front of Chet's Speedo down to below his balls, and Chet lay back in the seat and closed his eyes as Julio jacked him off. Angel kept taking looks at them in the rearview mirror as the cab sped down the coastal road and smacked his lips.

Chet ejaculated before they reached the beach, which turned out to be a gay nude beach tucked away behind and surrounded by coral rock outcroppings.

Chet lay on his back on a towel on the sand, while Julio, facing him, rode his cock. With some trepidation, Chet watched Angel appear at the edge of the beach, naked, with a cock that was thin but long, and move down the beach toward them, with arms and cock swinging in a way that made him look even more simian than before. He came around below Julio and Chet's feet, grabbed Chet's legs underneath his knees and raised and spread the legs while he rolled Chet's pelvis up. Julio didn't lose purchase on Chet's cock inside him but leaned his torso over Chet's, with the heels of his hands in the sand next to Chet's shoulders, bearing his weight, and captured Chet's eyes with his to watch Chet's expression as Angel slowly skewered Chet's channel with his long cock and pumped him in long strokes.

After they had rested, Julio and Angel carried Chet between them down to and into the surf. The stopped where the water was just above their waists, and Julio murmured to Chet, "You said you wanted to experience it all. Do you still want to do that?"

"Yes," Chet answered weakly. He didn't cry out and squirm when Julio, facing him, crouched and lifted Chet's body and lowered the young man's channel onto this cock, but he certainly did, grunting and groaning, and repeating "Oh, shit, oh shit, oh shit," as Angel embraced him from behind and worked his cock into the channel under Julio's and the two men counterpumped Chet from both sides in a double-penetration fuck in the rhythmically rolling surf. Chet whimpered and permitted himself to be moved about like a rag doll, but he took it.

The cab let Chet off by a bar under a tent near the pier where a party was in full swing, and Julio and Angel went off to a local bar for a victory round of beer.

Chet quaffed beer and danced with abandon on the crowded dance floor, where it was barely discernible who was partnered and who wasn't. It was the last day of Mardi Gras, which was celebration all across the Caribbean, and everyone was having a good, wild time. Chet became aware that he was being sandwiched between Margaret and Sheila in a dance. He suddenly didn't care. In fact, he suddenly had an idea borne of Steve's hectoring and what Pat had quoted from Benjamin Franklin about younger men and older women.

The two women were more than pleased and were anxious to get back to the ship as soon as Chet hinted what he wanted. The two took turns with him. He fucked Sheila first in the women's cabin, while Margaret patiently withdrew to the public areas of the ship, and then he fucked Margaret, with Sheila absent. He had insisted on this arrangement, because, while they were bent over the bed and he was fucking them from behind, he surreptitiously took the necessary photos with his cell phone, showing the line of his torso down to a half-buried cock between the woman's bulbous buttocks. Then a photo farther up their backs, showing their well-reconstructed, smooth backs and their luxurious flow of hair, of two different colors. They certainly didn't look their age in the middle of a fuck.

And Pat was right. They were experienced in making love to the cock. Sheila caught him taking the photos, but she thought it was a great idea. She let him snap photos as he took her from the front, with her lying on her back, arching her torso, and working her impossibly perfect melon breasts. She also was happy to let him click the cell phone as she knelt in front of him and cleaned his cock with her mouth.

He rather hated to take advantage of the women this way, but it was clear after they each had been with him for an hour, that most of the advantage being taken was of him by them.

Steve was so impressed by the photos and the spent condoms that he snapped his mouth shut and said not another word about testing or initiating Chet in the art of getting laid. None of the other fraternity brothers said anything either.

As the ship steamed out of Cozumel that evening for a return to Tampa after an additional full day at sea, Chet went on a hunt for Doug.

At the Rose bar, he was them together—Doug and Travis. And he saw them rise and both head up the stairs, toward the deck where Travis and Conrad's room was—where he himself had been bound and repeatedly fucked the previous day. There was no doubt in his mind by how Travis guided Doug with a hand on his elbow that it was Doug's turn to entertain Conrad—and that he was going willingly.

With a sigh of regret, Chet returned to his own room, turning in quietly, because Pat was fucking a curvy black woman in his adjacent bed.

* * * *

Confused, frustrated, and overwhelmed, Chet spent the entire next day avoiding all of the contributors to the "Chet gets laid" campaign so that he could clear his head and think about the experience and what it might mean for his future.

He couldn't think of anyplace better to hide than in that empty cabin on Deck 2 where Julio had taken him. He found the Nigerian room steward, and, for a price, Chet got the use of the cabin for the day at sea, the last day of the cruise. The Nigerian took his price three times over the day, fucking Chet to a glorious exhaustion. But when the Nigerian wasn't there, Chet was able to close his eyes, as he was spread-eagled on the bed, naked, and barely able to move between fuckings, to think. He knew now what he wanted, but he tried to think of the other options because what he wanted surely wasn't possible.

But it was possible, he found.

Buses from FSU met the returning university students on that cruise, by prearrangement, the next morning at the Tampa cruise terminal pier. As Chet was ready to get on the bus, he heard his name called.

"Chet, over here. Bring your gear over here."

Recognizing the voice, Chet turned in shock and walked over to the handsome man leaning against a Dodge Charger, his beefy arms folded over his bulging pecs, barely contained by his FSU T-shirt.

"Bud, what are you doing here?" Chet asked. "Chaperoning the busses?"

"Not really. I came in my car. If you're interested I can give you a ride back to Tallahassee. You won't have to go in a bus."

"Sure, Thanks. But what gives?"

"If you go with me, you'll be staying in Tampa for a couple of days, though."

"In Tampa?"

"Yes, with me. I have a hotel room and will fuck you into next Tuesday. And if you like that, I'll drive you back to Tallahassee and you can live with me."

"I don't understand," Chet said, tears coming to his eyes, and his body reacting in instant arousal. But it was just a dream. It must only be a dream, he thought. This is what he'd decided he wanted, what he thought it was impossible to have.

"Julio called me. He said that you were ready for me. Are you? I've been aching for you."

"Julio? Julio called you? You know Julio?"

"Yes, I know Julio. He initiated me on a cruise like this several years ago. Best thing that ever happened to me. When I knew you were going on this cruise, I asked Julio to arrange to work this one—and to work you. I know you want me, but that you just couldn't admit that to yourself. Julio says you're ready for anything now. So, do you want me?"

He opened the passenger door to the car.

"Need you ask?" Chet answered in wonder, as he slid into the passenger seat.