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.
