Caribbean Cruise Ch. 01: Future Shopping

The question was only about the timing; he didn't seem to be asking if I wanted him to fuck me again. My response to the two times he'd done so probably told him everything he needed to know.

"That would be fine," I whispered. That explained why it was my cabin. He had a wife on board. And, though I'd said it would be fine, I wasn't sold on the idea. I didn't want to be lost to Julio, no matter how pleasant the prospect. I was shopping for a younger man... for the future. An older married man wasn't anywhere in the plans. Still, he could fuck, and I hadn't had sex in a couple of months. But it wasn't what I was looking for.

But the fuck he'd given me was way much more satisfying than what Rod had been doing before he left me.

I looked up to tell him that maybe tomorrow night wasn't a good idea. We'd be in the Cayman Islands tomorrow night, half way through the cruise already. I had serious shopping to do.

But he was gone.

* * * *

I was moving a little gingerly the next morning when the ship had anchored off Georgetown on Grand Cayman island. We'd be tendered in to the shore and I had bought an excursion tour to snorkel the wreck of the USS Kittiwake off Kittiwake Beach, with an hour of beach time as well. So I couldn't sleep in. It wasn't just the vodka Collinses that had me creaking, it also had been the positions Julio had put me in and how brutally he'd fucked my channel. He wasn't built particularly big, but he showed no mercy in how he used his dick.

I had selected the excursion because there were, in fact, quite a few young, in-shape men on the cruise, and a snorkel and beach morning would provide an opportunity to shop and be shopped with stripped-down men.

I had withdrawn into my own thoughts and in locating and assessing various pains in my body over coffee and bakery items when I was distracted by movement at the next table over. It was the younger man from the dining room the evening before. He was dressed for a morning beach excursion. I had no idea whether I had sat down near him or he me, but we were sitting so that we were looking directly at each other. This morning he was looking as cool and "fitting in" as he had the night before. He was alone.

Our eyes met and he smiled. So I smiled back. But then both of us went back to our food. We glanced at each other a couple of more times, but when I finally worked up the courage to go over and sit beside him, I saw that he was gone. A bit later I saw him leaving the buffet line with a plate of food. He was, I was sure, taking it back to his cabin for his older companion.

When we were lining up for the separate excursions on the Georgetown pier, there he was, in my group. There were several other eligible-looking men on the tour as well, even ones that didn't seem to be attached. But my eyes kept going back to that young man, and I fancied that he looked my way occasionally too.

Once at Kittiwake Beach, the tour guide and his assistant staked out an area of the sand for us and we all rolled out our towels and disrobed down to our bathing suits. It was time to separate the possibles from the "also rans," and I intently checked out what was enticing. I also looked carefully at how the various young men were relating to other people. Were the other people young women or other men, or did they appear to be unattached and checking out other men? This had always helped me narrow down possibilities on cruises before.

Once again, it was hard for me not to check back with the young man from the previous night's dinner several times. He wasn't attached here; the older man wasn't on the tour, and, indeed, he couldn't have physically managed the demands of even getting to this beach. The young man wasn't checking out much of anyone, but I caught him looking at me several times. He also was a beautiful man when he was nearly naked. He was wearing a skimpy Speedo—as was I, because I was advertising as well as shopping. He wasn't as muscled as I was, his body being more lithe than muscle-bound, but everything was in perfect proportion—everything but the package that the Speedo couldn't hide, that is. The young man was hung.

He moved with grace, and I surfaced visions of running my hands over his smooth, tanned, and toned torso. There wasn't anything about this young man that I didn't like—other than that he already obviously was with an older man on the cruise.

Out we went snorkeling around the wreck of the ship that had been sunk off the shore specifically to help form a coral reef, which it was busy doing. The top of the ship was no more than four feet below the surface of the water. The coral loved it; the fish loved it; the snorkelers loved it. There was nothing not to like. I loved it too and was so engrossed in the wonders of life on a reef that it took me some time to become aware the young man I was interested in was swimming parallel to me. He swam like a dolphin. His body was as beautiful and he was as graceful under water as he had been on land. The urge to turn my attention to the bulge of his Speedo fought with the interest in exploring the coral-covered shipwreck with my eyes.

It wasn't long after I realized that he was swimming beside and not far from me that I was aware that he was gone. When I got back to the beach, he was gone from there as well. We all went up to the fringe of the beach to an open-air bar, where we all ordered drinks and then sat in the sun to dry off before the trolley car we'd come in took us back to downtown Georgetown. We still had three hours before we had to be back on board the ship.

At the beach bar I had chatted up a red-headed, muscular college guy who said his name was Chet and that he was a student at Florida State. He began to get skittish when we got to possibly available discussion, but I could tell that he was interested—just not sure of himself. He was with some other college guys, and as he drifted back into their orb, he allowed as how maybe we could meet for a drink on board in the next day or two. I noted him for possible cultivation.

After giving Chet some slack in the line if not removing the hook, I sat next to a hunky young black guy who said his name was just that—Guy. We waltzed around our backgrounds and our preferences and even nudged around to confirming that he was a top and I was a bottom when his boyfriend, coming out of the surf later than the rest of us, appeared. Guy introduced me to Tom, who also was young. The two of them were quite friendly, and Guy even mentioned that he thought threesomes were fun, but I didn't need yet another sexual experience that didn't lead to my future shopping goals. I was looking for one sexy, unattached, young man who could be domesticated and was still a top. A tall, order, I knew, but I had managed it before on cruises—if not for the long term.

After we were left off in the center of Georgetown, I walked two blocks back from the waterfront and found an upstairs bar I'd been told about by a friend who had vacationed in the Cayman Islands and probably knew all there was to know about gay hookups here. The islands weren't gay friendly, so everything gay was tucked away in corners.

I wanted to drown my sorrows—and steel myself for dinner when I'd be facing the young man I was interested in and his old sugar daddy across the room—not to mention Margaret and Sheila at my own table.

But I didn't have to do that. The young man was sitting at the bar of Pauli's, the gay bar that had been recommended to me. He saw me coming through the door and patted the barstool next to his and smiled.

I was trembling when I walked over to him. This short circuited a lot in whether he really was gay or not and whether he had any interest in me.

"Am I stalking you or are you stalking me?" I asked with a smile as I saddled up on the barstool. I'd pulled on an athletic T with deep armholes, but my shorts were in the bag I was carrying. I was still in my Speedo and wanted to be minimally dressed for the "shopping" I had anticipated to do in the bar, hoping to see some young guys from the cruise ship in here.

Travis was wearing about the same. That's what he told me his name was, right after he answered my question with, "I was rather hoping we were zeroing in on each other."

"I saw you in the dining room last evening," I said.

"I saw you as well. I got the impression that you were interested in me."

"You were with an older man. I got the impression that you had your hands full with companionship."

"That was Conrad. And, yes, we are a pair. Have been for some time. But we come on these cruises so that I can do a little cruising for myself. Conrad can take care of me in a limited way, but he's past having much of a sex life himself. He can manage something by watching, though, and I can jack a bit of satisfaction out of him if the conditions are right. So I put on a show for him occasionally. But to help me have full satisfaction, we go on these cruises a couple of times a year and I get my jollies. But maybe I'm giving too much information."

"No, not at all. So, you're telling me..."

"That I'm available and interested. I'm a top."

"And..."

"If you're looking for a top, I'm interested. We haven't been brushing by each other by accident."

"My name is Doug," I said, my hand shaking enough that I had to hold the beer glass that had just been delivered with both hands. "And, yes, I am a bottom. And also, yes, I'm very interested."

"Your cabin on the boat..."

"Is mine alone. I'm traveling solo."

"They have tenders going back to the ship constantly," he said.

I only got two gulps out of the beer before he was rising from his barstool and I was following behind.

Travis fucked me with my shoulder blades on the surface of the bed and my pelvis elevated on two pillows. He stood between my spread thighs, holding my legs up and out by fisting my ankles. He was horse hung, as I had already been able to tell, and enjoyed pumping me deep and slow at least at the beginning. It was what I liked too—that as well as the intensity of his stare and the expressions on his face as he leaned into me closely, his face less than a foot from mine. My wrists were tied together with one of my neckties and were hooked on the back of his neck. I was gagged with another necktie, which was a good thing, or my cries of passion would be heard all the way down to the center atrium. The bondage had been his idea. I thought it was kinky, but by the time we got there, I would have done anything to have him. Few men's cocks had been as deep inside me as his was. Few had coaxed me as open as he was doing. Few men had pulled moans as deep and long out of me as he did.

He had a regular pattern to his fucking—at least until he lost control at the height of lust, at which time he fucked with a fury as most young men his age did. He manipulated my legs, pulling them into his hips and bending them forward as he withdrew his cock and then pushing them straight out at arms' length as he glided deep again. He'd take three or four short pumps at depth or revolved his hips when he was fully saddled, which would make me moan and groan and then he would repeat the pattern.

His ejaculations were as strong and prolonged as only a young man at his peak can produce, and when he pulled the condom off the cock, its bulb was as thick with cum as a slug. I was panting heavily and he had barely broken a sweat.

After we had both come and cooled down, I opened a bottle of Malbec I had in the room and we went out on the balcony, standing close together at the railing, arms around each other, and talked.

Yes, I had loved the fuck, and he'd been happy with it too. No, I didn't mind the mild bondage. I'd found it arousing.

Yes, he was sure that Conrad knew what he was doing—and encouraged it.

The surprise though came when I asked about their arrangement.

"Conrad was in imports. He's retired now. I danced in Broadway shows but haven't done that for a couple of years."

"And he takes you on these cruises."

Travis laughed. "Rather the other way around. He wants me to go on the cruises. He even suggests I go alone, but I don't want to do that. I want to be with Conrad. And I pay for the cruises. He did support me for several years—he was always around, waiting for when I would come to him. But he doesn't get much out of his share of that business now. I came into money—a family inheritance. We live on my dime now."

I had been poised to proposition him. I was prepared to foot the bill of putting Conrad in a home if Travis came with me. But I could see now that there was a bond between the two that wasn't built on Conrad's finances. It was likely I couldn't break that bond—that I didn't want to—but, damn, why were all of the good ones already taken by lucky old men? Once again I was left high and dry. That was hard to take, especially hard because Travis fucked me just the way I liked it. I hadn't lied when I said I'd found the mild bondage extra arousing. I was depressed, but something in the back of my mind told me that I was missing something. I was just too sorry for myself to try to think of what that was.

"He was patient with me. I fucked a lot of men while I was with Conrad, even when he could manage it better himself. I fuck a lot of other men now," he said, with a laugh. "But at the end of the day, Conrad is there waiting for me."

I let it go at that, but I could see that he had finished his wine. "You know what I'd like?" I murmured.

This time Travis lay on his back on the bed and I rode his cock to another slow, deep ejaculation.

We talked about doing it again during the remaining two days of the cruise, but that night Travis and Conrad weren't at dinner in the dining room. Although the seating was prearranged, this night the other four seats were occupied by two middle-aged couples. But there were no Travis and Conrad.

I roamed the public areas of the ship after dinner—after having thought up another halfway plausible explanation on why I couldn't choose between Margaret and Sheila to bestow my sexual and other favors on. It was midnight before I saw him. He was walking up the stairs toward one of the cabin floors with the red-headed college student I had started to proposition at the tour on the Grand Cayman beach, the one named Chet. So much for either one of them satisfying me this evening or being further pursued for longer-term possibilities.

I went straight to the lounge at the top of the ship, where Julio was waiting.

"I thought you wouldn't come," he said as I lowered my body in the chair next to him and ordered a vodka Collins.

"I wouldn't miss being with you again," I said. And at that moment I meant it.

He fucked me on the carpet of my cabin, taking me hard and furiously, as if it would be our last time, both of us making sounds of animals in high heat. And, as it turned out, it was our last time.

When he left me that night, Julio said that, unfortunately, this had been our last assignation. The bridge nights didn't run the last night of the cruise. He wouldn't be free of his wife the next night. As good as his fucking was, I didn't regret that it couldn't go on for another night. Not only did it leave me exhausted and bowlegged, but it just wasn't the right arrangement for me. There was no future in it.

I took another beach and snorkeling excursion the next day when the ship docked at the pier in Cozumel, Mexico. However, even though there were several hunky young men on the tour—and a few who showed interest in me—this future shopping had all become rather hollow for me. I could sense that was so, but I just couldn't understand why. I kept thinking of what Travis and Conrad had together, and wishing that I was Conrad. But I wasn't, and it would be terrible of me to try to break into what they had. I knew if I had such an arrangement and someone took my young man away, I'd want to slit my wrists.

This time the young redhead named Chet sought me out and danced around the possibility of the two of us hooking up. He had waited too long to work up the courage. The timing was just bad. I let him off the hook as gently as I possibly could.

Travis and Conrad weren't at dinner the last night of the cruise, but Travis did find me in the wine bar.

"Conrad is interested in you," Travis said, as he settled in the chair beside me. "I told him what a good lay you were."

"Interested in me? Interested in what way?"

"I told you he liked to watch."

And so he had, I thought, with a bit of shock. I hadn't zeroed in on what he meant at the time, though.

"He wants to watch us having sex?"

"Yes, it's the only way he can halfway get hard. It's what I do for him on these cruises. It's the enjoyment he gets out of these cruises—watching me fuck other men. You don't have a problem with that, do you? You're so hot, I read you for a swinger."

"No, of course I have no problem with that, but I don't think I'm available this evening," I said. I had to give this some thought. This was a blind alley as far as my goal was, but the thought of doing it was making me hard.

Travis didn't wait for an explanation why, even though my mind was racing trying to provide one. He already was looking around and rising from the chair beside me. "Well, then, sorry I can't sit and chat. I have to be a man on a mission. It's what Conrad is back in the room expecting."

"Good hunting," I said and raised my glass to him. I wasn't resentful, but I was a little sad. I also was somewhat relieved, feeling that I had dodged a bullet of some sort—at least until I gave it some thought.

He was only three steps away from me when I had given it sufficient thought. "Wait, a minute, Travis."

* * * *

My shoulder blades were on the edge of the bed and my head was hanging over the end. I was watching the waves of the sea the ship was plying through, half way between Cozumel and Tampa, from an upside down. My arms were arched to the floor, my wrists bound by Travis' belt. He was on his knees between my thighs, my pelvis raised on three pillows. He held my right leg out to the side, my left leg running up his torso, the ankle hooked on his shoulder. He was fucking me deep with his cock and was stroking my cock with one hand and working my nipples with the other.

The old toad, Conrad, was sitting in a club chair between the bed and the balcony door. He was grunting, and pulling at his cock, while, through slitted eyes, he watched Travis fuck.

I was close to coming. I had never done this before and quite possibly would never do it again. But it was a good fuck to end the cruise with—to end the whole idea of picking up men for the future through cruising.

* * * *

Thursday morning, Sol was waiting for me in his car at the side of Channelside road at the Tampa cruise terminal pier. I had gotten off the ship a couple of hours later than I expected, but there he was, waiting for me.

"Was it a good cruise? Any luck?" he said, as I put my bag in the trunk and walked around to the driver's window rather than the passenger door.

"The cruise was fascinating. I think I was lucky, yes."

He looked around with a quizzical expression as if, if I had been lucky, he expected me to have a young man in tow. I took advantage of him looking around to put my head in the driver's window, cup his head in both hands, and bring his mouth around for a kiss.

"What...?"

"During the cruise I decided I knew what you really meant when you said you'd be here waiting for me," I said. "I regret to say I didn't discover that on my own. Dunce that I am I had to have help."

Sol didn't ask me what I meant. That alone told me that I had been right. That all of this time he had been waiting for me.

I went around and climbed in the passenger seat. "Let's go home, Sol. Take me to the future."