Dylan Thomas Merriweather III Ch. 01

This is an original work of fiction. Any resemblance between the places and persons described below and actual places or persons is coincidental. All individuals who engage in sexual activity (which is male on male) are over 18—as should be any reader. This is a three-part series, all written at this time. Copyright 2023, all rights reserved. BD

A young sailing entrepreneur returns home from Greece

Meet "DT" Merriweather

Dylan Thomas Merriweather is the current head of the family business. His family, being of Welsh origin, had named him after the famous melancholy Welsh poet-drunk, Dylan Thomas. He is only 34, but both his grandfather and father had died in a storm-related private jet crash in the Appalachian Mountains four plus years ago, leaving a thriving business and two massive key-man life policies. He, being the only boy-child of the oldest son (his father), and already being groomed to lead the family and its businesses, immediately assumed the top job. Perhaps fortunately for Dylan, he had managed to conceal that he was gay until after their death, or they might have tried to disinherit him. They were very conservative, strait-laced WASPs with very old and set ideas and most likely were irredeemably homophobic. But that was no longer a concern. He was CEO and he now held a majority of the voting shares (thanks to performance bonuses paid in options over the last few years)—and he was definitely. although discretely, now out.

His ancestors, over generations, had built a multi-billion dollar mining conglomerate—moving from coal and iron, to copper and precious metals and most recently, to cobalt, lithium and other rare and valuable minerals. Dylan knew very little about mining (although at daddy's insistence, he had taken several college level geology courses), but he knew finance, and he knew the Wall Street world of mining finance, options trading, and the quick-step world of buying and selling companies and commodities.

In just the first year, he had increased profitability by 30%--and free cash flow had similarly increased. Subsequent years showed similar gains. The family, originally bent on selling the company immediately after the death of the patriarchs, had soon recognized Dylan's talents and killer instincts. So they let him go for awhile. (Actually, the estate put him in control so there was little they could do anyway.) The other heirs were now happy to clip coupons or reap dividends, let him run the company (from wherever), and look the other way at whatever lifestyle he chose to lead.

Dylan's first love was boating—preferably by sail. At the family's estate on Weems Creek, near Annapolis, Dylan currently maintained and occasionally sailed an ultra-modern Italian-built 70' single-mast, turbo motor sail catamaran—which he had equipped with every imaginable technology to make it possible for only two to handle although he kept a crew of four on payroll. He called it the Evermay II (May, being one of the best sailing months in the Chesapeake each year). This was a fourth-generation yacht equipped with GPS, wind, tide, and wave sensors and servo-motors to make it as "self-sailing" as possible—although Dylan rarely actually sailed these days.

In fact, it was so self-sufficient that Dylan had had it built to hold a smaller 22' sailboat (without mast obviously) in the aft hold-starboard pontoon—so he could "really sail" when he had the time. The yacht had four staterooms, all equipped with king beds, including an owners' cabin that was palatial and a tech office that could be the command center of any major corporation. Crew quarters were forward and below, reached by a separate gangway and contained in the large windowed port pontoon, thus providing privacy for Dylan and his guests when desired. Crew quarters were very nice (and he paid well)—so Dylan had little trouble attracting the kind of guys he wanted as crew.

Before his Dad's death, he had sailed on the family yacht (an ancient America's Cup contender) several weekends each month in the Chesapeake during season, a few weeks each winter in the Carib or the South Pacific, and typically another few weeks in the Med in July or August). Then, his father's untimely death required his presence 24/7 at corporate headquarters. So, Dylan very quickly opened a "branch headquarters" in Annapolis and announced his office would normally be there. He commissioned the building of the Evermay II in Genoa.

Then, he had begun to form his team of managers, keeping some of the veterans, but bringing in new minds with new ideas. His goal was to move Weather Mining (his great-grandfather had often said that there was very little "merry" in mining and refused to use the full family name for the company) to one he could run with trusted managers, monthly board meetings and electronic communications. His intention: stay on Evermay as much as possible and run the company from shipboard. As a consequence, he had installed the most elaborate communications and internet devices with flawless cloud security. COVID had conveniently accelerated the strategy.

Dylan was gay—and out, which made him a unique figure among mining executives who were mostly aggressively hetero, macho males who had played rough contact sports at various state colleges and kept multiple mistresses around the world. His gaydar was well-developed, and he often suspected that under the militant homophobia of several of the top execs was a bi-curious sub, waiting to be opened and dominated. But, for the most part, he avoided "industry" events—typically golf weekends that involved quasi-legal discussions about pricing "policies" followed by drunken parties and hired female companions.

Dylan was a graduate of Choate and Harvard, a preppy dresser, blond, crew cut, tanned and in shape. He was small—about 5-10 and 165 lbs (2' inches of his height and 20 pounds from his senior year)—and his features were fine, some would say "aristocratic"—which essentially meant that his nose was long and thin and his eyes were clear blue. No blemish had ever dared to mar his handsome face. He had been a rower (he had once even rowed competitively at the annual Henley Cup as coxswain because of his small size) and a swimmer and thus had slim, lithe muscles. So at mining executive meetings, he stood apart—and was the butt of many locker room jokes. But, his competitors underrated his intelligence, tenacity, and vicious alpha "business killer instinct" at their peril. He was a talented shark—gobbling weak but promising competitors almost at will.

Once or twice after a post-acquisition drunken celebratory event, when he had been particularly offended by homophobic comments made by the other CEO, he had seduced and then "acquired" the cherry of the other chief executive or one of his lieutenants—penetrating a quickly lubed ass with his oversized dick. In that department, he was clearly all-man and gifted. None of his conquests ever dared to make fun of him again.

Dylan was the exact opposite of his namesake. He knew his alcohol limits, was rarely in a funk, and was in control of every aspect of his young life. And of course he was not the maudlin womanizer! But, he was fond of poetry—and often quoted apt lines during and after sex.

In business Dylan was a "master," but in his personal life, he was a confused young man, socially inept, a little timid, self-conscious—all of which he covered with a convincing command bluster. He had lost his mother before he was even a teen; then his father's death had abruptly interrupted his playboy initiation. Neither parent had showered him with attention or love—just expectations and rules. A grandfather had set a different example: a rough entrepreneur who had secret mistresses in various places, a "family man" who had little regard for family. By his teens, Grandpa was supplying girls, beds, and condoms.

Emotionally, Dylan ran hot and cold—often the stoic hard businessman, more often the needy young man searching for love. Being gay didn't help. As a wealthy, attractive young guy, girls (and even a few cougars) had surrounded and occasionally pawed him, trying to break through his shell of shyness and reserve. But, he knew almost from the beginning that he would only find what he was looking for in someone of the same sex. Until a few years after after Harvard, he was not willing to risk himself, to put himself in a position to meet potential partners, to become vulnerable to emotion, let alone love—or to risk his father's wrath.

After his father's death, Dylan changed. He outed himself. Then he decided to put himself in the "line of fire"—that is, live and work in a place where he could meet and be met by guys. He was going to crack the shell himself. He had always liked Annapolis. It was full of young, attractive, clean-cut males from the Academy, St. John's or crew from the large yachts that anchored in the harbor. Even though most of his Academy partners had a desire for sexual anonymity, Dylan knew that statistically 10% of them were gay, and perhaps another 10% were at least bi-curious—even before the "Don't ask, don't tell" rules were abolished.

Dylan knew the bars they liked—and an invitation to sail and party on the yacht or at the mansion was legendary and almost always accepted. If sailing was his first love, partying with attractive young men quickly became his second, particularly those with a uniform. Starting in September, he hosted regular parties at the mansion on Saturday and on the yacht on Sunday, moving to the mansion only in winter. At the beginning, Dylan used his wealth, the mansion and the boat as "guy-catchers"—afraid of rejection if he put himself out as "just plain Dylan." Slowly, he began to gain confidence in himself and his personal life—as his business successes multiplied. But, he remained steadfastly fearful of commitment, although he typically settled on a BF and fucking partner by Thanksgiving each yera.

He was mostly a bottom, but given his out-sized dick (named "DT" by his partners, a cute word-play on "JT" or John Thomas, the name given by Lady Chatterley to her lover-ardener's enormous cock) which almost matched his out-sized ego, he was often persuaded (or decided) to top—while rocking on board a moving sailboat, stretched out in the sun on one of the double lounges in the prow of his yacht, or in his beautiful suite at the old family house. There was always a tension: he was a bottom, but his business persona almost demanded that he be a top. So he moved into the role of "control bottom."

Curiously, the Annapolis place had once been his grandfather's "pleasure palace" (where he kept his mistress) away from business and home in Baltimore. Now it was his--and definitely dedicated to pleasure although of a slightly different kind. In five or so years, Dylan had changed from a shy, closed-up kid to a successful male predator—but the emotional quotient had not yet reached the same level within him. He kept his emotions in a bottle on the shelf. Emotionally he was a young male teen—insecure, playing games to win, dominating partners, keeping quiet about feelings.

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It was late August. Dylan had just returned from several weeks in Greece. Afternoon winds on the Chesapeake would soon pick up and with them, the occasions for parties on the Evermay. He had the e-picture "book" of the new midshipmen and a similar "new students' e-directory" from St John's and was circling his favorites. For him, these were Sears e-catalogues of potential partners in pleasure. But, his gaydar didn't work infallibly in print. So Dylan picked out those that appealed, memorized their names, and planned to cruise at several Annapolis night clubs in the next few weeks. He would then begin hosting a few "private and small" weekend parties at the Annapolis mansion and on Evermay to scope out and capture his prey. The parties had become annual events and were well-known among the LGBTQ+ community. Rumors from upperclassmen (together with Twitter and Grindr notes) would serve two purposes: anyone invited would want to attend the blow-outs; anyone invited would know Dylan was gay and looking for partners for that night or future parties and sails. In the past, such parties had produced both playmates and medium term relationships. And he wanted both by the end of September. It had worked for him before. So why change the strategy?

Only last June, Dylan and Ollie (Oliver Bell Perry) had ended a school year semi-exclusive relationship when Ollie graduated, accepted his naval commission and was posted to San Diego—both agreeing that long distance relationships didn't last. They both knew that rapid advancement within the US Navy, even now theoretically tolerant of bi/gay lifestyles, just didn't happen for "out" gays. Perry's family was all navy; there was no other option. Dylan was sorry to lose one of the nicest guys he had ever met, one of the few for whom Dylan actually felt affection, (and one of the largest, most talented cocks that had ever plundered his ass), but he knew others existed. He knew from the beginning that Ollie was not marriage-bound—at least not to him. But, it did depress him a bit to have lost his first real love. Of course he loved the hunt. And the novelty. He'd get over Ollie. Or at least so he told himself.

Meanwhile Dylan had brought home a souvenir from the Aegean waters—a 30 year old "pilot" who had been hired to assist his own crew with the treacherous navigation and anchoring in the ultra-deep waters around the Dodecanese Islands. They had met when Dylan was sailing the "little Evermay" one afternoon. Both were in skimpy bikinis. Greg expressed interest and Dylan accepted. He was soon hired. In addition to helping the staff navigate and anchor, Greg had also been navigating Dylan's chute with his prodigious staff and anchoring deep inside his small, muscular ass. Greg was tall for a Greek, about 6' and extra-ordinarily handsome—with dark short curly hair, dark eyes, and a small flat nose set in a square face. He was deeply tanned, strong, and muscular, with one of the smallest bubble asses that Dylan had ever seen. He was, of course, hung, uncut, a skilled cocksman, insatiable and without any taboos whatsoever. He went with and "did" males and females as often as he changed his tee. Dylan particularly enjoyed his deep-anchoring and his rough manhandling, and didn't need to fear commitment.

Greg had been "tested" before employment—like all of Dylan's employees, so they went bareback from the start. So after a few weeks of non-stop, mind-boggling sex in the Greek and Turkish waters, Dylan had decided to give him a bonus—a month long trip to the States, with accommodations, of course, in Dylan's massive bed—to tide him over until a new Annapolis-based partner could be found and landed.

The sailing season in Greece was nearly over. So Greg handed over his tour captain responsibilities to his younger brother who had been handling their jointly-owned sailing yacht during Greg's absence, and flew to the States with Dylan. Conveniently, Dylan's captain was entitled to a few weeks of vacation and needed to do a refresher course at the Coast Guard. So Greg slipped into the open spot.

Dylan Begins His Seasonal Search

Just as Dylan checked the last potential photo-invitee to his party, Greg reached over, pushed the lap top away to the floor, and pulled Dylan into his lap. He didn't ask. He never asked. He just took what he wanted when he wanted it. Lube was at the ready and soon so was Dylan. Greg raised him up easily with his powerful arms, hardened with years of rowing, hauling and anchor-pulling, and slowly lowered him onto the massive cock which they had named Andy (short for the Greek, Andros, a powerful all-masculine phallic symbol). Dylan's legs easily surrounded Greg's narrow waist and he pulled himself into Greg's lap, deepening the penetration.

Dylan felt his cavity stretching to accommodate the now familiar tenant and then his smooth ass cheeks landed on the massive shaved balls. He began to dance on the larger man's lightly-haired chest, nibbling on his hard tips. Greg squeezed his cheeks and pushed them together to enhance the tightness of Dylan's chute as he repeatedly lifted and impaled Dylan. After a few minutes of this foreplay, Greg rose, gripped Dylan by his soft cheeks, shuffled to the bed, and easily dropped the pair on the still-open bedding. Soon he was pumping, hard and deep, using the rolled down hood of his uncut cockhead to stimulate Dylan's pleasure spot—while he held Dylan tightly and licked, kissed and caressed his ear lobes, neck and shoulders. Dylan pulled his ass closer with his legs. "Deeper Greg. Harder. Yesssss. Bite me." Greg reached up and pinched the already-swollen nipples, then used his lips to draw them out even more painfully. Then he plunged again.

Dylan was a vocal and responsive bottom. He reached around and his fingers circled Greg's rim, ultimately penetrating to the love spot. Greg's eyes widened and he pounded harder, as Dylan whispered, "Like that, huh? I think all Greek boys are born with hungry assholes and hard dicks. I think I might do you this afternoon." Then he moaned in pleasure as Greg erupted. Feeling the gush of hot liquid deep inside, Dylan too spurted. Greg, being well-schooled in ancient history, liked the image of a volcano: an explosion, and eruption, then hot liquid flowing and caking lava on their torsos. He was good. And Dylan loved being handled. And this was definitely a very active, hot-lava-spewing volcano.

Both knew this arrangement was not permanent—neither apparently cared--, but Dylan had enough power (and money) to retain Greg as a play-toy and fuck-buddy-dildo for so long as he continued to pleasure the young master. Greg might appear to be the dom—he certainly was bigger in every respect, but Dylan was really the master of the games. Fortunately, Greg proved to be the ever-ready rabbit, ready to screw (or, more rarely, be screwed) at a moment's notice—and for as long as desired. He knew not to become attached to Dylan—or his luxury. He was the kind of guy who enjoyed every day (and night) without expectations, ready to top or bottom—in short a man of many pleasures, but few demands. But knowing and doing were different things—Greg was falling for Dylan, and he knew it. But, he already understood that Dylan didn't respond emotionally to many. He knew their relationship was still transactional and mechanical.

The upcoming cruising and parties would presumably provide Dylan with other partners for the coming winter—and perhaps, but unlikely, even a soul-mate favorite. Greg would be returned to his friends—just a little richer and likely a little bit sad. But Greg knew that he would never be the "one" for Dylan.

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Cruising at the Pink Pelican Club

On the Saturday of Labor Day weekend, Dylan decided to introduce Greg to Annapolis society—at least that part of Annapolis society which congregated at the Pink Pelican Club—a large bar, eatery and dance club, located well outside the historic district. In fact, the place looked like a decrepit ship's store warehouse—a large, air-conditioned, grey metal building in the warehouse district. Except for the club, the entire neighborhood was nearly deserted after sundown. And the Club was marked only with a small neon pink pelican at the apex of the A-frame and the double pink doors in the alley. Inside, was very different: it was lively, attractively lit, with a long mahogany bar, beach memorabilia, and a large dance floor. Booths lined one wall, some with curtains that could be drawn for privacy. It was one of three "clubs" in Annapolis, but probably the nicest and certainly the gayest.

They dressed in club appropriate duds (tight tees, tighter black jeans, and dock-siders) and uber-ed to the warehouse. They both planned to drink and the Maryland Highway Patrol and the local Annapolis police were particularly vigilant on weekends in and around the city. The time was 11:30 and the club was already crowded. Dylan was known to the bouncers, and after perfunctorily showing his ID, paying the small cover, and placing their phones in small lock boxes (no selfies here), both guys were admitted and went to the bar. Despite the holiday weekend, there was no live music, only disco, and dozens of guys were pairing off on the dance floor. Many were already shirtless and sweaty. Jeans and shorts tended to be tight. But not so tight as the clinches of many of the dancing pairs. And not so tight as to prevent an occasional hand dipped inside to grip a prize. The whole floor throbbed with sexual energy.