Gaycruise Daddy

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“It’s a great way to throw your money away; that’s what it is.”

“Well, let’s see, Pete. How much have you spent on the site’s hookup service, and how many guys have you actually hooked up with?”

“I’ve had some real hot conversations and cybersex with some of them,” Pete sniffed.

“Purely in cyberspace, right? At, what, a dollar a word?” John answered, with a snort. “And I’ll bet the photos they showed weren’t any more of them than yours are of you.”

“But three K at a single throw?” Pete retorted. “Just to go out in the ocean and back and watch young men fuck? And there won’t be any hiding behind a fake photo for you, either. You’ll have to be in a Speedo, or you’ll stick out like a beached whale.”

“The boat’s going to Bermuda. We’ll get off in Bermuda. I’ve never been to Bermuda. And, besides, I’ve got a good enough body,” John answered indignantly.

Pete wheeled his office chair from beside John, where both had been staring into John’s computer screen, and made a big deal of pushing his glasses down on his nose and giving John a sarcastic stare. That tableau held for about ten seconds.

“Well, I do for a man my age. Certainly better than yours.”

“OK, I’ll grant you both of those.”

“And I bet I’m hanging lower and thicker than most of the young guys who will be on the cruise too.”

“I’ll grant you that too. But there’s no chance any of the guys on the boat are even going to get an opportunity to see your—”

At that point Pete broke off because he saw one of the cashiers, Julie, standing in the door to the grocery store manager’s office and looking pained. John noticed the change in Pete’s demeanor, and his face swiveled toward the doorway.

“Yes, Julie, what is it?” John’s fingers went instinctively to his keyword and toggled the screen from the homepage of the Gaycruiser gay male dating site to the chart of last month’s inventory statistics at his Baltimore branch of Krogers.

“A display got knocked over at the end of aisle three and there’s pickle juice running on the floor and it doesn’t look like Eddie’s gonna get it cleaned up any too fast. He’s already slid and fallen in it twice.”

John took a deep breath and let it out in a sigh. “Thanks, Julie. Pete, could you—?”

“Hey, don’t look at me, I’m management,” Pete interjected. But he was already struggling to his feet.

“Yeah, but you’re lower management and I’m upper management.”

“Middle management,” Pete muttered as he followed Julie’s retreating figure through the floor and down the corridor to the main store floor.

What John was muttering at the same time as Pete walked away was, “Bermuda’s gotta be better than this—and watching young guys fuck on a cruise ship will be a whole lot better than on a computer screen anyway.”

* * * *

John was riddled with mixed emotions—nerves, arousal, a bit of dismay—as he stood in line waiting to register with the clipboard-laden, Speedo-clad tour director at the bottom of the gangplank up to the sleek, small Poseidon’s Spear, the cruise ship that was to take him two days out and two days back to Bermuda from Baltimore at the top of the Chesapeake Bay.

It was true, as he had actually hoped, that he was the only fifty-something man standing around waiting to get on the ship. The up side, though, was that the other men there were almost universally young hunks he would love to sink his dick into.

The cruise was one of the ones offered by the Gaycruiser Web site on a quarterly basis that augmented their on-line dating service. The fees were stiff, but the Web site no doubt thought that charging sixty men cruising for hookups on their site for the added hookup chance of four days out on the ocean on a sleek yacht where clothing was optional and fucking like bunnies was actually encouraged helped their paid membership statistics. Especially as extra money could be made from selling videos of the cruises on sex sites.

The cruise was going to be extra expensive for John. He had something of a plan—and there wasn’t much of anything else in his life to spend money on. So, he’d reserved, and paid a high premium for, one of the suites on the ship. And before arriving, he spent weeks in the gym. His muscle tone was fine—for his age—but he had needed to get a little less thickish around the middle, and he’d at least partially succeeded at that. As he approached the cruise ship from the stern, he’d done a mental comparison of his torso with that of the Poseidon depicted on the fantail, and he didn’t think he came off that badly. A man in his fifties had to be expected not to have a willowy figure. He’d had his gray hair styled and highlighted in a shimmery silver that caught the light and the loose hairs plucked from all of the unattractive places so that what was left on his chest was a pleasing—at least to him—patch that trailed intriguingly down his belly to his pubes, which he’d also had trimmed and shaped. He’d left curled tuffs in his arm pits, enough so that they wouldn’t give the gaziantep swinger impression they’d been purposely shaved. And he’d spent enough time in a tanning both for a sort of all-over tan so that he wouldn’t look like the office worker that he was when he got to the ship’s pool.

And he’d bought some spiffier, expensive-looking clothes at the Tanger Outlet near the Chesapeake Bay Bridge. He’d been lucky to find a Speedo with sort of a bull’s eye design on it that would help emphasize his best feature—his thick, eight-inch cock.

When he got up to the tour director, a well-built hunk with blond-highlighted curly hair with a chiseled face and a practiced smile, he opened up his gambit.

“Ah, and you are?” the young man asked dubiously, looking down at his clipboard after a quick look up and down John and a slight sniff of his nose.

“Jonathan Pender. From Baltimore. Although, I’m not sure what home base was given you when the reservation was made. It could have been the Hamptons or Aspen too, I suppose.”

The cruise director’s slight supercilious smile had already started to turn more respectful as he found John’s name on his clipboard, but, hearing what John said, he looked up with a far more welcoming—and interested—look on his face. John was also pleased to note that the men immediately behind him in line had stopped whispering to each other and were more attentive now too. At least they had stopped snickering.

“Yes, well it does say Baltimore, and I see that you are booked into the Neptune suite.” This latter discovery had been the reason the tour director’s attitude had already changed. “May I be the first to give you a hearty welcome aboard. My name is Tony and don’t hesitate to ask if there’s anything—absolutely anything—I can do to make riding . . . riding the waves a greater pleasure for you.”

The young man fluttered his eyelashes and held out his hand for a handshake that held for several seconds longer than fully necessary and felt, John thought at the time, a little strange, because the young man had folded a finger inside the traditional grip and rubbed it across John’s palm.

For a moment John wondered if this was some sort of signaling in the world of men who liked men—and he supposed that he should have spent more time researching on the Internet.

“It notes this is your first cruise with us, but I certainly hope it won’t be your last.”

“Yes, well,” John answered, with a sigh. “The Hamptons usually are the best place at this time of year. But with the house refurbishing . . . well, I thought I’d try something a bit different.”

“We can certainly offer you something different here, sir,” Tony answered in a coquettish voice. “If you don’t mind, I’ll seat you at the captain’s table for dinner tonight.”

“That would be fine,” John answered in a tone he hoped would convey that it was no more than what he would have expected anyway.

On his way up the gangplank, John was congratulating himself. He thought that was an auspicious beginning. And he hadn’t even lied about anything. There always could have been a mix-up in listing his home in the reservation, the Hamptons no doubt were delightful at this time of year, and surely some house there was being renovated.

He gave a little chuckle, looking forward to pleasures to come, if he was lucky and clever. As he entered the ship, the first thing that caught his eye was an etching of Poseidon rising from the sea, with his trident a thick column rising between two meaty balls and ending in three hard-phallus points. He chuckled at this too.

He didn’t do much chuckling that afternoon as the ship was steaming south down the center of the Chesapeake Bay and then turning southwest out to sea. As he had expected, all life gathered around the pool on the top deck in the center of the ship and most of the cruisers were starting their festivities early with drinking, cavorting in the pool, and sucking and fucking on the lounges. There were very few inhibitions to be seen and many an arousing distraction to watch. The young men were almost uniformly gorgeous, and the rewards for a voyeur were high.

As much as John liked watching, it was obvious that the young men weren’t flocking to him. He had donned the bull’s-eye Speedo and taken a prominently displayed lounger and laid a towel over his less-pleasing bits, but no one—with the occasional exception of someone doing a double take when seeing the line of his curled-around cock inside the Speedo—was paying much attention to him.

This changed a bit at dinner. He had to admit to himself when he looked in the mirror that he looked quite distinguished in his rented tuxedo. There was something about a tuxedo that brought out the best in a gray-haired, mature man, and John said a little prayer of thanks to the hair stylist he’d gone to rather than his regular barber earlier in the week.

The captain might not even have known that John was at the table that evening. The cruise director obviously was under strict orders to seat the most meltingly beautiful submissive young man on the cruise beside the captain on the first night, and they had not even made it to desert before they all had to rise when the captain did so as he escorted his entertainment for the evening from the table and to his cabin.

The cruise director obviously had similar plans for John. John had been conveniently seated next to Tony, and during their dinner conversation, Tony pumped John for background information, and John ran the thin line between being from a famous family of retailers and being the manager of a Kroger grocery store branch. John must have done it successfully and Tony must have heard what he wanted to hear, as, while those left at the table were being served coffee, Tony laid his hand in John’s lap under the table—and, John was pleased to hear, gave a little gasp—and asked John if he could come to the Neptune suite later in the evening.

It was at this point that John knew that his scheme and the money he had invested in this cruise were going to pan out. When the cruise had come up on offer and while Pete and he discussed what young men seemed to be looking for when they played the hookup game on the Gaycruiser Web site, John reasoned that there were three reasons a young man would fuck a stranger. One, the stranger was a young hunk. This left John out, he readily acknowledged. But there were two other, more hopeful reasons. One was that they were looking for a good fucking and the last—the biggest reason by far, John thought after researching the traffic on the dating site—was that they were looking for a sugar daddy who would take care of them in the manner in which they would like to be accustomed.

Of the three, John saw his greatest hope as being the good fuck, because he had been magnificently endowed and had had decades of practice before his opportunities began to thin out as he aged, dwindling to nothing but memories soon after he pushed by fifty. Unfortunately, as John grew older, fewer and fewer young men who he fancied had stuck with him long enough to enjoy what he could give them down deep. And then John thought about the sugar daddy angle. He reasoned that if he got into it before others discovered the opportunities it accorded, he just might be able to play the sugar daddy card long enough to get his dick inside a couple of these studs and subdue them to begging for him. At that point, John thought, the good fucking might become as important to them as the sugar daddy aspect.

And, eureka, before Poseidon’s Spear cleared Hampton Roads and was sailing out into the Atlantic, John’s research assured him that he was the only one on this cruise who looked and acted the part of a sugar daddy—apart from the forties-something captain, who had his own entirely different avenue for dipping his wick as he pleased.

John left nothing to chance that evening. When he answered the knock on the cabin door and determined by look through the keyhole that it was Tony, as expected, John had the lights out, music with a jungle beat going softly and subliminally in the background, and all he was wearing was a silver silk robe, open in a swath at the front that followed the line of his sculpted chest hair down to his sucked-in belly and then on down to where his proudly displayed penis and balls reached for the floor. The only light was what was coming from the corridor with the door open and a filtering of moonlight through the gauze draperies at the balcony door.

When the cabin door was closed and Tony was kneeling between John’s knees as the grocery store manager sat on the edge of the bed, there was little light, and all Tony could concentrate on with astonishment and lust was John’s engorging dick and the glorious difficulty—for both of them—with which he was soldiering to get it all in his mouth.

And the night had grown even darker when John laid back, stretched full length, on the bed and let Tony ride a cock that he had to work hard, with great groans and grunts and cries of passion, to accommodate. John showed him too, now that the atmospherics had been equalized and the rhythm of the beat of the music in the background was becoming more intense, that John’s hands were not too old to massage Tony’s cock in quite pleasant ways while he rode John’s master phallus. This was something that many years of experience enhanced. A man of John’s age and experience knew how to please another man—at least in the dark and with a thick, eight-inch cock. And a man of John’s opportunities was far more attentive than a younger man would be to his partner’s needs.

After working Tony’s cock up, John moved his hands to the young cruise director’s waist and tilted him slightly toward John’s chest. At the same time John raised his knees between Tony’s thighs, spreading Tony’s thighs, and rolled his own pelvis forward. The head of his cock moved down to the pleasure spot inside Tony’s channel that a seasoned expert like John knew was there. Tony cried out in never-before-felt pleasure as John’s cock head rubbed across Tony’s prostate once, twice, three times and then, as Tony gasped, plunged deep inside him, only to drag slowly back up his channel walls. Tony fisted his own cock and beat it to the increased intensity of the specially selected jungle music in the background. Rub, rub, rub, plunge, drag; rub, rub, rub, plunge, drag. And Tony soared over the moon and came in profusions of cum such as he’d never experienced before with a younger man. And then when Tony thought it was over, rub, rub, rub, plunge, drag. John had had years to perfect being able to hold off and to prolong.

Hearing Tony’s moans was all John needed to know that a man with real experience was good to have on a fuck cruise.

When he left the cabin slightly before dawn, Tony seemed quite pleased with the two hundred-dollar notes John pressed into his hand after patting the sweet, tight buttocks he had had the pleasure of splitting a second time after Tony had recovered from his first hour-long ride on John’s cock.

The young cruise director must have spoken of the highlights of the experience the next morning, as John hoped he would, because when he came out to the pool and settled on a prominently placed lounge, he wasn’t alone for long. Several young men gathered around him, asking about life in the Hamptons and Aspen and seeking advice on stocks and bonds and then, standing and posing for John and asking whether this or that muscle needed more definition or whether their tan lines showed too prominently. John laughed when one asked if he could dispel the rumors and see John’s most important muscle, but John didn’t give out easily. He teased them along while taking the opportunities as they came to cop a good feel here and there.

And they were ever so grateful when John was willing to rub the suntan lotion on them, particularly the young man wearing nothing who thought perhaps his cock might also burn if it was left uncovered and who lay there on John’s lounge chair, John sitting at his waist, and smiled and arched his back and slitted his eyes and moaned as John expertly, forefinger pressing into piss slit, brought up the young man’s own white fluid to spread on top of the tanning lotion on his cock.

When the saucy young drinks waiter brought back John’s tequila sunrise, he asked the older man if there was anything else he needed in such a nice way and with his fingers tracing John’s cock through the bull’s-eye Speedo that John, at last, let him bring his phallus out into the air—which was especially good for John, as now all eyes were on that and he could stop sucking in his stomach and stretching to tighten up his pec muscles. As the young man lowered his mouth over the bulb of John’s cock and started flicking John’s piss slit with his tongue, John sighed in satisfaction and reached for the proffered cock of a deliciously divine chocolate young man sitting close to him on the neighboring lounger.

“I would very much like to take this lovely cock elsewhere,” the waiter murmured to John after John had come and he was still slowly stroking John’s cock. “May I come to your room tonight, Mr. Pender?”

“Alas, Emilio,” John said, trying to feign a face of deep regret but saying the words with the greatest of pleasure, “I have three engagements already this evening. And there are limits to what I can do. I do have an opening or two on the return trip from Bermuda, though.”

John knew he was on top of the world, though, when, as he was departing the pool area—and right out there at midday, under the sun, rather than in a dark cabin—the delicious young man the captain had no doubt fucked the previous night came up and begged to ride John’s cock—right there and then. John picked the sweet young thing up and settled his butt down on the flight of stairs going up to the bridge—where he could see the captain watching them. The young man licked his lips and spread his legs and hooked his heels over the railing at each side, as other young men gathered around, their eyes locked on the weapon John was wielding between his legs. All sighed—not just the beautiful young man—as John slowly fed his cock inside him and changed the angle so that his bulb was planted on the young man’s prostate. Rub, rub rub, plunge, drag; rub, rub, rub, plunge, drag. The young man cried out in ecstasy and writhed under John’s masterful attentions, and all of the other young men around murmured and fisted their own cocks.

John went on forever—rub, rub, rub, plunge, drag—and the gorgeous young man whimpered and weakened and started to babble and his legs went to rubber and other young men had to lean in to hold them up and out as they gazed down at the root of the thick cock moving in and out of the puckered hole—shallow, shallow, shallow, deep, draaaagg back to the sound of a weak moan. The young man came but John didn’t stop. He was tired, but this was lesson time, his time to make his point. Rub, rub, rub, plunge, drag. Rub, rub, rub, plunge, back, plunge, back, plungebackplunge, and the young man cried out as he came again with John. Moans all around as one by one, all the other young men came too.

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