Forward
A few years ago, a reader reached out to tell me how my story “Pook & Pete” had resonated with him personally. He related strongly to the character, Pook, and shared that Pook’s relationship with Pete resembled his attachment to his therapist. He asked if I would write his story and after dozens of email conversations, his experience became the basis for “The Singlet”, posted in Spring, 2024.
Recently, the same reader came forward and shared even more in-depth insights about himself with the request I use his experiences as inspiration for another story. Although the plotline is fictional, the desires and kinks are his. This is his story.
Chapter One
Summer of 2008
The moment that would define Josh forever came on a summer afternoon shortly after turning 13.
Josh’s father was a successful CEO with an unyielding work ethic shaped in part by his experience as a first-generation Japanese American. He had a deep respect for precision, perseverance, and restraint that fueled his drive for excellence. But he applied that intensity to business success, not child-rearing. Determined that his son be raised fully “American,” he prized conventional markers of masculinity: football scores, rough-housing, clean, uncomplicated toughness. He had every expectation that Josh would embody the American version he admired.
It wasn’t to be.
Throughout his youth, Josh had felt unmasculine. He was bookish, quiet, and had little interest in conventional team sports. He wore his father’s disapproval like a waterlogged cloak.
Josh’s only refuge was his neighbor Jake. Three houses down, two years older and about to enter high school, Jake was the older brother Josh never had. Swimming was Jake’s world and his dad, Caine, a charismatic Australian, would be his high school swimming coach in a few weeks. Josh had only met Jake’s dad, Mr. Barrows, a handful of times, but there was something about him that made Josh’s young heart pound. An Olympic Bronze Medalist for swimming butterfly, he moved to the U.S to study law, he was every bit the former Australian Olympic athlete. At least 6’2” tall and lanky with bushy blond hair like he’d just stepped off the beach, with a wingspan of 6’7” rivalling Michael Phelps. Sadly, Jake’s mother had died in childbirth and raising Jake alone, while juggling a demanding legal career, made him heroic in Josh’s young eyes.
That afternoon, Jake invited Josh to swim with him and his father at the high school where he somehow found the time to volunteer coach. “He’ll give you some tips,” Jake had said casually. “If you’re thinking about swimming seriously, you should take him up.”
Josh and Jake biked to the high school to meet Jake’s dad and before he knew it they were in the locker room getting ready. It smelled of chlorine and echoes. Josh was still tugging nervously at the strap of his bag when Caine appeared—tall, assured, utterly at ease in the space.
Seeing Josh, he greeted him warmly by ruffling his hair and—with his magnetic smile—said in his easygoing Aussie accent, “Ah, young Mr. Tanaka. There’s our future Olympic medal winner. Great to see you again, mate.” Just that simple greeting made Josh’s heart pound. And then, without ceremony, he peeled off his sweats, leaving him only in a simple racing Speedo, black and unadorned, revealing a body that Josh had fantasized about without even knowing it. Josh had never seen Jake’s dad in anything other than street clothes. Late 30s, tall, massively broad shoulders tapering to a narrow waist, crazy-long muscled arms and pecs honed by years of discipline, abs that had never tasted dessert, and legs that were pure muscle. Josh nearly lost his breath when his eyes passed over the bulge in his Speedo. It wasn’t massive, but it took every ounce of willpower not to stare. The irony wasn’t lost on Josh. It was the only part of the body that needed to be concealed but the tiny piece of Lycra drew your eyes directly to it. The body part that was most forbidden was most on display.
Something aligned inside Josh with startling clarity. This wasn’t just attraction, though it was undeniably that. It was presence. Command. Authority. And inescapable desire…or something else, he didn’t know. But it was real.
In the pool, Mr. Barrows was deliberately patient. Via Jake, he knew Josh’s father was an unyielding tyrant, leaving Josh desperately in need of love and reassurance. He corrected Josh’s stroke with calm instructions, guiding hands that lingered only as long as necessary. Each brief brush of skin sent a chill through Josh, electric and grounding all at once. Caine spoke of control, of breath, of motion, of knowing when to push and when to yield. Josh absorbed every word, somehow aware that he was learning more than technique.
Caine felt something too; not sexual, but paternal—yearning to be the guiding light this young man needed so badly.
What struck Josh most was how natural it felt to be steered. How right it felt to be ordered. How he relished being controlled. And how much he wanted to please. Mr. Barrows embodied something Josh had been searching for without knowing it—a commanding strength that invited surrender.
That afternoon changed each of their lives in a way neither could’ve predicted. Caine’s gentle authority, his dominance, and, yes, his Speedo fused into a moment that would only become clear much later in life. And Josh’s yearning for authority would haunt Caine for many years to come.
2021 – Stone & Ash; Day 1
26-year-old Josh Tanaka stood across the street from Stone & Ash LLP and let the moment land.
The building rose cleanly from the sidewalk—steel, limestone, glass—modern without being flashy, confident without apology. It was exactly what Josh had imagined a firm like this would look like: precise lines, deliberate restraint, money that didn’t need to announce itself.
He adjusted the strap of his backpack, checked his watch, and confidently crossed with the light.
Inside, the lobby smelled faintly of polished stone and coffee. The concierge checked him off the list, and within moments he was rising toward the firm’s upper floors, surrounded by other recruits in tailored suits and neutral expressions.
Josh felt calm. Focused. Ready.
Stone & Ash hadn’t been his only offer out of law school, but it had been the one that mattered. The firm’s reputation for rigor, selectivity, and institutional power had made the outreach feel less like an invitation and more like a summons. He’d accepted without hesitation.
And no—despite what anyone might assume—Caine Barrows had nothing to do with it.
Josh had been aware, of course, that his high school swimming coach and Jake’s dad was a senior partner at the firm. Anyone in the city who paid even cursory attention to high-stakes litigation knew the name Caine Barrows. But Josh also knew enough about corporate culture to understand that nepotism—even indirect—was poison. He’d never mentioned the connection during the recruitment process, and as far as he knew, Caine had no idea he’d even applied.
That was how Josh preferred it.
The first two days passed in a blur of orientation sessions, HR presentations, compliance briefings, and carefully choreographed introductions. The firm took its onboarding seriously. Stone & Ash did nothing casually, least of all the cultivation of its junior talent.
On the afternoon of the second day, they were ushered into a conference room overlooking the river. Floor-to-ceiling windows framed the city like a model—orderly, controlled, purposeful.
A managing partner stood at the head of the table.
“As you know, one of the defining aspects of Stone & Ash,” she said, “is our mentorship structure. Every incoming associate is assigned a senior partner mentor—someone responsible not just for your work product, but for your professional and personal development.”
Josh straightened almost imperceptibly.
“Your mentor will supervise you, sponsor you, and advocate for you. The length of the mentorship varies. Some relationships last months. Some last years. Some have resulted in lifelong friendships. That depends on you.”
A pause, deliberate.
“Your mentor will seek you out after orientation concludes.”
Josh felt a flicker of anticipation he hadn’t expected.
By the morning of day three, Josh had an office. It wasn’t large, but it was real—a door that closed, a proper desk, shelves waiting to be filled. His name was already etched neatly on the door. Seeing it there sent a quiet thrill through him.
He was arranging a framed photo—him on his law school graduation day—when he sensed someone standing just beyond the threshold.
Josh looked up.
Caine Barrows filled the doorway.
For a fraction of a second, the world seemed to narrow. Probably around 50 now, Caine looked older than Josh remembered, but if it were possible, even more handsome. His blond hair had grey throughout and was now cut neatly; his posture still ramrod straight. He wore a charcoal suit that fit like it had been expertly tailored to showcase his physique.
His presence was immediate. Commanding. Unmistakable.
Josh stood so quickly his chair bumped the desk.
“Mr. Barrows—”
“Caine,” he said, smiling faintly. “You can call me Caine now, mate.”
The smile didn’t soften him so much as focus him. It was the same expression Josh remembered from the pool deck years ago—measured, warm, and entirely in control.
“I rather hope I’m not interrupting,” Caine continued, stepping fully into the office.
“Not at all,” Josh said, his pulse inexplicably loud in his ears.
Caine closed the door behind him—not sharply, but decisively.
“I wanted to introduce myself properly, and to let you know that I’ll be serving as your mentor.”
Josh blinked.
“I—” He stopped, regrouped. “I’m honored.”
Caine studied him for a moment, eyes sharp but not unkind.
“I want to be very clear, I had no involvement in your recruitment. When I heard your name, I recused myself entirely. Given your history with my family and me as your coach, that was non-negotiable.”
Josh nodded. He’d expected nothing less.
“That said,” Caine continued, “I was pleased to see you on the list. Your college scores, your LSAT, and least of all your outstanding college swimming career all point to what an exceptional candidate you are. The committee was unanimous.”
Something in Josh’s chest loosened.
“But there’s more”, Caine continued, his voice dropping as if were now speaking privately. “I distinctly remember you from your high school swimming career. Your dedication, your drive, and most vividly, your desire to please.”
Josh was taken aback that he’d made such an impression. And his mention of Josh’s ‘desire to please’ came as a complete—but not unwelcome—surprise.
Sensing Josh’s puzzlement, Caine continued, “I’ve never coached—in swimming or professionally—a person who gave of himself more than you. That’s a rare quality—and it will get you far.”
Josh said nothing, but the expression on his face was one of relief, as what Caine said seemed to ring true.
He continued, “Only after everything was finalized did I disclose that you and Jake were friends growing up and my role as your coach, and I asked to be considered as your mentor—if you were comfortable with it.”
“I am,” Josh said immediately, trying not to appear overly eager.
Caine’s mouth curved slightly.
“Good.”
They sat.
For a few minutes, the conversation stayed light. Caine asked about law school, about Josh’s move back to the city, about his parents. It felt strangely intimate, sitting across from him like this—professional now, equal in some formal sense, and yet not.
Josh reciprocated about with questions about Jake and how Caine was getting along as a bachelor.
Then Caine shifted.
Subtly. Deliberately.
“Now,” he said, folding his hands on the table between them, “let’s talk about expectations.”
The temperature in the room seemed to change.
Caine’s voice didn’t rise. It didn’t need to. It sharpened instead—precise, authoritative.
“I expect the same excellence and commitment here as I saw in the water,” he said. “Preparation. Responsiveness. And most important, commitment to my expectations. If you’re unclear about what they are—you ask.”
Josh felt the words land in his body as much as his mind.
“You’ll be staffed on my clients immediately,” he continued. “I don’t coddle. I invest. If you’re here, it’s because I know you won’t disappoint me.”
Josh nodded, every instinct aligning toward that standard.
Caine watched him closely, as if measuring not just comprehension but reaction.
“We’ll meet twice weekly. Every Monday morning, first thing to discuss the week. Strategy and process. Then Thursday night over dinner. That’s when we’ll discuss your development, both professional and personal. The degree to which you are—or aren’t—meeting my expectations”.
Josh hesitated just long enough to notice that the invitation wasn’t phrased as one.
“I understand,” he said.
Caine stood.
“Welcome to Stone & Ash, Josh.”
As Caine left the office, Josh remained seated, heart still racing.
The shape of his future had just changed.
And he knew—deep in his bones—that disappointing Caine Barrows was not an option.
2018 – Six Years Earlier
As 20-year-old Josh was beginning his second year of college he was confident and athletic, but only tentatively crawling out of the closet. His father was askance at Josh’s dedication to swimming, largely due to the tiny Speedos his son and the other swimmers wore, confirming his suspicions that Josh was gay. The only thing that mitigated his disapproval was Josh’s success at the sport and how his physique had matured as his swimming career progressed. Josh was quickly becoming a man. Not the man his dad had hoped for, but a man, nonetheless.
And although Josh hadn’t officially come out to his parents, they seemed to know, but said nothing. It was a classic case of “don’t ask, don’t tell.”
Josh made the varsity swim team his freshman year and was immediately a standout performer. His success was driven by pure talent as well as the perseverance and intensity he’d inherited from his father. What no one saw coming—least of all his father—was how his physique had matured. Coach Barrows had started Josh on a weightlifting and nutrition regime in high school and it was accelerated in college as his new coach mandated a rigorous 12-month training program. Only 30 days into the new program, Josh could begin to see results. His shoulders broadened, his biceps and pecs took on real definition, his abs flattened and hardened, his waist appeared to shrink, and his legs took on a musculature that amazed Josh. Six months into the regime, just as the season was to begin, Josh looked like a new person. Wearing only his assigned competitive Speedo, he looked at himself in the mirror and saw a sexy male fitness model—the type that had earlier confirmed his interest in men. What Josh couldn’t explain was that his skin had somehow obtained a 24-hour sheen. Previously, his yellow/brown skin had self-consciencely set him apart, made him “different”. Now it appeared to glow, accentuating his muscle definition and making him the center of attention at every swim meet and beyond.
Josh had been elevated into the A-team of college athletes, and he knew it. For most of his life, he’d been an unathletic, scrawny little Asian boy, for whom sex—let alone aggressive man-on-man sex—simply wasn’t in the cards. What he saw in the mirror told him the exact opposite. A man other men would desire, even fight over.
But there was one element of Josh’s new sexual confidence that haunted him. As his sexual life fitfully progressed, he found himself attracted almost exclusively to submissive sexual roles which were at odds with the masculine image he idolized. His porn search history was nearly all young, masculine men being dominated by older men in authoritative roles. From 1-1’s to small groups to gang bangs, he identified with the young man being used, being flogged, being punished, even being gangbanged. He struggled to make the two images—the muscular, athletic swimmer and the submissive sex toy—coexist.
Given his college was in a large city, he began to pursue these interests, albeit with considerable caution. Using the internet, he identified the local gay bars and researched which would best fit his interests. No surprise, he landed on The Eagle, particularly Friday nights—leather night. He couldn’t afford their full leather gear, but he had tight jeans, a leather jacket and bought himself a pair of leather boots that matched the bar pics online.
Using a flimsy excuse one Friday night, he made his way to The Eagle around 10PM, open leather jacket, shirtless, very tight jeans (which did little to conceal his near erection), and boots. He’d obtained a credible fake ID through a college source and, with his heart pounding in his ears, walked in as nonchalantly as he possibly could. He was carded ordering a beer, was surprisingly casual about producing it, and the night began.
He leaned against the bar and scanned the dimly lit interior. Up to this point, he had been concentrating exclusively on simply being served, he’d barely notice what he now saw. Dozens, maybe even hundreds of hot, gay men of every age, in every combination of leather dress (and undress), dancing, flirting, aggressively making out. He knew he needed another beer to calm down so quickly downed the first one and ordered another. About halfway through that one he got the courage to leave his safe space at the bar and circle the room. Of particular interest was a dark hallway off the back of the large bar space out of which he saw guys disappear and later re-emerge. Given his robust porn history, he assumed it was a dark room, but he had to see for himself.
On his way, he couldn’t help but notice the admiring stares he was receiving. He didn’t realize it, but he was fresh meat, in the best possible way. A young, muscled, sexy-as-hell Asian with glowing, almost incandescent skin that looked like it’d been oiled for a photo shoot and begged to be man-handled…or worse.
He arrived at the mystery door and took a couple steps into this new world. He had two simultaneous reactions. The first nearly took his breath away. He easily envisioned himself on his knees servicing any one of these massive cocks, or in the sling getting both holes worked by strangers. His mind went there without a second thought. However, his second reaction was more circumspect. He realized, rightly, that he wasn’t ready for this. He had to walk before he could run. He hadn’t earned the right to be in a room like this, pleasuring men like these. But he knew the day would come.
He pulled himself back out to the bar and continued his journey around the perimeter. He spotted a second bar he hadn’t seen previously, slightly out of the mainstream, and easier to inconspicuously sip his beer and observe. He snagged the lone bar stool, planted himself there, and let the night unfold. Into his third beer, his nerves finally calmed, and he almost felt like he belonged there…like he was “one of them” as he gazed out on the dance floor.
He was in his own world, oblivious to who was on either side of him, until he felt a firm hand on his shoulder and the presence of someone in his ear. “You are one sweet boy” the low, gravelly voice pronounced. Trying desperately to appear cool, Josh slowly turned to see the face behind the voice, and, to his delight, the rugged gentleman was straight out of a porn fantasy. A 40-something bear with greying hair, beard and chest fur, a massive, muscled body, and full leather.
Without thinking, Josh uttered, “Thank you, sir”. ‘What the fuck have I done?’ he thought to himself. With those three words—"Thank you, sir”—he had confirmed his interest and his submission."
Clearly sensing the boy’s inexperience, the leather man took it slow. “You don’t have to thank me for simply stating the truth. You’re a beautiful boy” he uttered as he tenderly brushed his cheek.
Josh was having an out-of-body experience. Every fantasy was playing out in real time, but he knew he had to go slow. He’d used good judgment by ditching the back room, he needed to be equally judicious now.
“That’s very nice of you to say sir”…damn, there it was again…”You’re very handsome yourself.”
“No need to reciprocate the compliment, but thank you, my boy. Mind if I call you ‘my boy’” he asked.
“Of course not” Josh blushed.
“Then let me buy my boy a beer” and motioned to the bartender for another round. “And by the way, my name’s Richard. My friends call me Ridge. You can call me Sir.”
“Yes, Sir, my name is Josh.”
Now face-to-face with their knees touching and a fresh beer in their hands, the leather man proposed a toast, “To my boy” he smiled.
Josh, not breaking eye contact, responded, “To Sir”.
What had just happened, Josh thought to himself. He put himself out there, clearly laying out his submissive role. But Ridge was being exceedingly careful to earn Josh’s trust as his inexperience was as obvious as his barely worn leather jacket.
Ridge guided them through a friendly, non-threatening, and revealing conversation in which Josh shared his story…his rigid father, his scant sexual experience, his untested proclivity toward submission. Sir finally had to ask, “So you’re really a virgin?”
“Yes, Sir, I am”, Josh blushed.
“Do you want to stay a virgin?” Sir continued,
Josh took a deep breath, looked Sir straight in the eye and answered, “No Sir.”
“That’s what I thought”. He paused for a few moments as if he were contemplating what came next and finally asked, “Josh, do you trust me?”
Josh looked down to his lap, then up back into Sir’s eyes and answered, “I want to, Sir. Can I?”
Sir smiled and placed this hand on Josh’s cheek and replied, “Yes you can, boy. I promise you, you can.”
He continued slowly, but with great authority, “Josh, do you want to taste another man? Suck another man’s cock? Savor another man’s hole? Feel a man’s cock inside you?” Pausing, he added, “Serve another man?”
Josh’s heart leapt, “Yes! Yes! Yes! And FUCK YES!!!” Josh cried, trying in vain to contain his enthusiasm.
Sir let it sit. Then grasped Josh’s two hands and said quietly, “You’re coming home with me. I’ll go slow. I promise I won’t do anything you don’t want to. You’ll leave a new man. A real man.”
Josh squeezed both Ridge’s hands with both of his and simply replied, in a whisper, “Yes, Sir.”
-To be continued-
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