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The Tailor's Apprentice

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John is 32 and has been unemployed for 6 months, fired from a manual labour job when cutbacks were being made. John is a typical straight man, muscular, but a little chubby, hairy and barely groomed. He has messy dark brown hair, a moustache and stubble and bright blue eyes with an easy, charming smile. He is 6ft tall, with great posture and a large cock and balls. John's only real interests in that 6 months have been working out, smoking weed and masturbating, his favourite pastimes. But his wife has had enough. Don't come back without a job, she'd said that morning. We meet John as he is wandering the city, feeling lost in many ways, as he turns into an unfamiliar, dark little street. Part way down he notices a sign in a dusty looking little shop, hiring. It's a tailor's. We follow John on a journey of how far his boundaries will be pushed, how much he will do for a well-paying job, and his discovery of an underworld of sex between men, behind the fusty and formal front of bespoke menswear.

Chapter 5: Morning Rituals

John woke to warmth. A deep, wet, sucking heat around the head of his cock. He groaned, eyes still shut, the haze of sleep and the previous night’s exertions clinging to him. He didn’t need to look. The rhythm was unmistakable—Silas, working him with a devotional focus.

He forced his eyes open. Morning light, grey and diffuse, filtered through the lace curtains of Silas’s bedroom. Silas was nestled beside him under the duvet, a silhouette of concentration. All John could see was the crown of silver hair moving in a slow, deliberate bob.

The technique was different from the night before. This wasn’t the hungry, sloppy worship or the deep, challenging stretches. This was clinical, educational. Silas took him deep, his throat opening in a practiced swallow that made John’s toes curl, then retreated to just the tip. He swirled his tongue around the corona, tracing the ridge with pinpoint accuracy before plunging down again. Each descent was a fraction deeper, a fraction more controlled.

“Fuck, Silas,” John rasped, his voice gravelly with sleep.

Silas pulled off with a soft pop. He emerged from under the covers, his glasses on the nightstand, his black eyes clear and focused. “Morning,” he said, as if they were discussing the weather. He spat a glob of saliva onto his palm, reached for John’s cock, and began to jerk him with a slow, twisted grip. “The frenulum is particularly responsive in the morning. The nerve endings are rested.”

He demonstrated, using his thumb to rub small, firm circles just beneath the head. Electric pleasure shot up John’s spine. “Jesus Christ.”

“Precisely,” Silas murmured, a faint smile touching his thin lips. He bent again, this time ignoring John’s cock entirely. He licked a slow, broad stripe from the base of John’s ballsac up to the tip. He took one heavy testicle into his mouth, suckling gently, his tongue a relentless, soothing pressure. He switched to the other, his hand still working John’s shaft in that twisting, up-and-down motion.

The dual sensation was maddening. The tender, almost aching fullness in his balls, the slick friction on his cock. John could only lie back, one arm flung over his eyes, and let the waves of pleasure crash over him.

“I’m gonna come,” he warned, his hips beginning to stutter.

Silas released his balls and took him back into his mouth, deep, all the way to the root. He held him there, his nose buried in John’s pubic hair, his throat convulsing gently around the head. He stayed perfectly still, just the faint, involuntary flutters of his gag reflex massaging the most sensitive part. It was too much. John cried out, his body bowing off the bed as he emptied himself in pulsing jets down Silas’s willing throat. Silas swallowed diligently, his adam’s apple bobbing, until John was spent and soft.

He cleaned John with a few efficient licks, then settled on the pillow beside him. They lay in silence for a while, listening to the distant sounds of London waking up—the groan of a bus, the shout of a market vendor.

“I have a fitting at ten,” Silas said finally, his voice back to its usual baritone calm. “A demanding client. You’ll observe. It’s a different kind of performance.”

John just nodded, his body humming with a deep, satiated peace.

Down in the shop, the atmosphere had shifted. The intimate, shadowed opulence of the west room and the cluttered warmth of the flat were gone, replaced by bright, clinical light and an air of severe professionalism. Silas was no longer the voracious lover or the patient teacher. He was Mr. Blackwood, Tailor.

He moved with an inhuman precision. His hands, which had so intimately explored John’s body, now handled mohair and silk with the same detached reverence. He spoke little, issuing brief, quiet instructions. “The basting thread, John. The shears. Stand here, observe the drape from this angle.”

The client, a sleek man in his fifties with the cold eyes of a banker, was being measured for a morning coat. Silas’s touch was impersonal, efficient. His fingers flew with a tape measure, noting figures in a small leather-bound book. He discussed apexes and breaks and risers with a fluency that sounded like a foreign language. John stood silently by the mirror, holding a tray of pins, feeling like an impostor in this world of quiet, extravagant perfection.

When the client left, promising to return in a fortnight, the silence in the shop thickened.

“You see?” Silas said, not looking at John as he meticulously coiled a length of measuring tape. “It is a transaction. He pays for perfection. I provide the illusion of it. The garment will be flawless, but it will hang on a frame of avarice and insecurity. I clothe the man he wishes to project, not the man he is.”

“And what man am I?” John asked, the question out before he could stop it.

Silas finally looked up. The professional mask softened, just a fraction. “You are the man who does not yet know what he needs to project. Which makes you refreshing. And exhausting.”

He led John to the worktable in the back room. “Today, you learn the fell stitch. It is invisible from the outside. It is what holds the facing to the interior, what gives structure without revealing the means of support. It is the most honest stitch.”

For hours, John worked under Silas’s exacting eye. His large, clumsy fingers fumbled with the fine needle and silk thread. He pricked his thumb, swore, bled onto a scrap of muslin. Silas didn’t chide him. He simply demonstrated again, his own movements a ballet of economy. “It is not about force. It is about direction. A gentle persuasion of the fabric.”

As John’s stitch length began to even out, Silas spoke, his voice low. “I wasn’t always here, in this shop. I learned my craft in a different place. A… stricter house.”

John kept his eyes on his work, sensing the confession in the air.

“There was a man there. The master tailor. He believed discipline was the highest form of care. A misplaced stitch was corrected not with words, but with a thin leather strap across the knuckles.” Silas held up his own hands, turning them over. The skin was flawless. “He had other disciplines. For… restless apprentices. He believed in draining the body of its baser urges to focus the mind.”

John glanced up. Silas’s gaze was distant, fixed on the wall but seeing something else entirely.

“He would take us into the cutting room after hours. He called it ‘evening prayers.’ We would have to kneel. Service him. And then one another, under his instruction. It was brutal. Efficient. It was not about pleasure. It was about control. About making the animal function of the body as mechanical as a buttonhole.”

The needle slipped again, grazing John’s finger. He sucked the small bead of blood away, the metallic taste sharp on his tongue.

“I hated it,” Silas continued, his voice barely a whisper. “And I craved it. It wired my pleasure to submission, to performance. For years after I left, I could only find release in transactions. In paying men to use me, or to be used. It was empty. A beautifully constructed garment with nothing inside.” He finally looked at John, his black eyes gleaming. “Until now. You are not a transaction, John. You are the first honest thing I’ve held in a very long time.”

The weight of the confession sat between them. John didn’t know what to say. He reached out, his work-rough hand covering Silas’s slender, perfect one on the table. “Your stitch is better than mine,” he said, lamely.

A genuine smile broke across Silas’s face, cracking the solemnity. “It had better be. I’ve had more practice.”

That evening, the quality of their intimacy had changed. It was slower, deeper, infused with the day’s revelations. They shared a bath in Silas’s old, claw-foot tub, steam curling around them. Silas sat between John’s legs, his back against John’s chest. John washed him, using a soft cloth to soap the narrow shoulders, the pronounced spine, the arc of his ribs.

He lathered Silas’s silver hair, massaging his scalp. Silas leaned back, his head resting on John’s shoulder, his eyes closed. “No one has ever done this,” he murmured.

“What, given you a wash?” John teased gently, rinsing the soap away with a cupped hand.

“Cared for me. After. The men from before… they left. Or I left. The act was the entire point.”

John kissed his temple. He slid his soapy hands around Silas’s front, across his flat stomach, down to his cock, which lay soft in the water. He didn’t stroke him to hardness, just held him, weighing him in his palm, feeling him slowly begin to swell. Silas let out a shuddering sigh.

Later, on the rug before the fireplace, Silas laid John down. He didn’t mount him or suck him. He simply explored. He kissed the thick pectorals, lapped at John’s nipples until they were hard pebbles. He nibbled the soft flesh of his love handles, his stubble scratching the sensitive skin. He worshipped the sheer physicality of John, the hairy, muscular, almost chubby reality of him.

“You feel so real,” Silas breathed into the skin of John’s stomach. “So substantial.”

He moved lower, his tongue dipping into John’s navel, making him jump and laugh. Then he pushed John’s thighs apart. He didn’t go for his cock or his balls. He nudged John’s legs up, knees toward his chest, exposing him completely.

John’s breath hitched. This vulnerability was still new.

Silas just looked, for a long moment. “Beautiful,” he whispered. Then he leaned in and began to lick, not with the hungry intent of the night before, but with a curious, mapping tenderness. He licked the perineum, kissed the inside of each thigh, nuzzled the heavy sacks. He pressed a soft, closed-mouth kiss directly to John’s hole, making him gasp.

“Relax,” Silas murmured. He spit, a thick glob that landed with a warm splat on the pucker. He used his thumb, not his tongue, to smear it around, to press gently against the resistance. “This isn’t for me. It’s for you. To feel everything.”

He pressed and circled until the muscle softened and yielded, allowing the pad of his thumb to slip just inside. John moaned, a deep, resonant sound. Silas worked him like that for minutes, opening him slowly with fingers and spit, stretching him with a patient, relentless gentleness that was somehow more intense than the fisting he'd performed on Silas the night before.

“Now,” Silas said, his own cock hard and leaking against his belly. He positioned himself. He pushed in slowly, so slowly John felt every millimetre of the invasion. He was bigger than his thumb, thicker than his tongue. The burn was there, a bright, stretching fullness, but it was subsumed by the overwhelming sense of being connected.

When he was fully seated, he didn’t move. He folded himself over John, chest to chest, and buried his face in John’s neck. They stayed like that, joined, breathing together. John could feel Silas’s heartbeat against his own, a frantic flutter that gradually slowed.

Then Silas began to move. It was a rocking, a grinding, not a driving fuck. Each slow retreat and slide home brushed John’s prostate, sending warm shocks through his groin. John wrapped his legs around Silas’s waist, pulling him deeper. He kissed Silas’s mouth, tasting himself, tasting the night.

“You feel…” John searched for the word as Silas rocked into him, hitting that spot with unerring accuracy. “You feel like mine.”

Silas’s rhythm faltered. A sound like a sob caught in his throat. He fucked him then, harder, deeper, his precision shattered by emotion. “I am,” he gritted out, his voice breaking. “Oh, god, John, I am.”

Their climax was simultaneous, a silent, convulsive merging. Silas spilled inside him with a choked cry, and the pulsing heat was the trigger for John, who came between their pressed stomachs in thick, hot streaks, untouched.

They lay tangled on the rug, the fire dying to embers. The room smelled of sex and sandalwood and honest sweat. John’s phone, silent for days, buzzed insistently from the pile of his clothes across the room.

Both men heard it. Neither moved.

The buzzing stopped. A moment later, it began again, a persistent, angry drone.

Karen.

The real world, with its demands and frustrations, was on the other side of that screen. John held Silas tighter, pressing his face into the silver hair. He could feel the shape of his own life, ill-fitting and coarse, waiting to be put back on. The perfect, honest stitch of the last few days was over. Now he had to decide what kind of garment he was going to sew himself into. The phone buzzed a third time, a dying insect shudder on the hardwood floor. Silas didn’t flinch. His breath was a warm, even tide against John’s collarbone.

“You should answer it,” Silas said, his voice muffled by skin.

“I know.”

He didn’t move. He counted the seconds of silence after the buzzing stopped. Twenty. Thirty. The fire cracked, spitting a final ember onto the hearth. John exhaled, a long, deliberate release of the peace he’d been holding. The decision crystallized, not with drama, but with the simple weight of fact. His old life was a poorly drafted pattern. Here, with Silas, he had found the correct grain.

“I’ll call her tomorrow,” he said. The words hung in the dim air, a vow. “I’ll sort it. I need to be here.”

Silas lifted his head. His black eyes searched John’s face, not for lies, but for the cost. “What will you say?”

“I don’t know.” John shrugged, the movement shifting Silas against him. “The truth? That I’ve found a new life. An apprenticeship. That it requires my full attention.” It wasn’t the whole truth, but it was a thread of it he could pull without unravelling everything. “My needs are here now.”

A complex emotion flickered across Silas’s features—relief, guilt, a fierce pride. He nodded, once, and laid his head back down. “Then you are mine.”

The next morning, over strong coffee and the meticulous ritual of preparing the shop, the previous night’s commitment settled into a new practicality. John watched Silas align bolts of fabric, his mind working on a different problem. The acts they’d shared—the fucking, the sucking, the deep, shocking penetration—were a language he was learning. But one dialect remained intimidating, a territory mapped only in brief, intense forays.

“The fisting,” John said, the word still foreign and thick in his mouth. Silas paused, a length of charcoal-grey wool in his hands. “I need to understand it. Not just… doing it. The limits. Where it ends.”

Silas placed the wool down, his precise movements never faltering. He turned, leaning against the cutting table, and regarded John with that teacher’s gaze. “It ends where I say it ends. The boundary is my voice. My body will always try to accept more. The mind must govern.”

“But what’s the goal?” John pressed, stepping closer. “You said you need to be filled. Where does that need stop?”

A faint, almost ethereal smile touched Silas’s lips. He looked not at John, but through him, to some private horizon. “The goal is the extremity itself. The feeling of being so utterly opened that the self dissolves. I have taken a hand, many times. I want to know what lies beyond the wrist. The forearm. To feel the slow, impossible stretch of the sigmoid colon. To see if I can take a whole arm.”

John felt a jolt, a visceral clench in his own gut. The image was at once medical and mythical. “A whole arm? Jesus, Silas. That’s…”

“It is,” Silas agreed, his focus snapping back. “It is not for today. Or tomorrow. It is a destination. The journey requires patience. The tissue must learn, must bloom slowly, like leather worked by hand. Rush, and you tear. The basics, as you said, must be mastered.”

John absorbed this. The sheer scale of the want was humbling. It wasn’t mere perversion; it was a pursuit. A craftsmanship of the body. “Show me the basics again. Properly. Talk me through it. I don’t want to just shove my hand in you. I want to do it right.”

They left the shop in the care of a closed sign. The west fitting room, in the flat grey daylight, looked less like a boudoir and more like a surgical theatre. Silas laid out tools: two new bottles of clear, viscous lubricant, thicker than anything they’d used before; a folded towel; the graduated silicone toys from the lacquered chest.

He undressed with methodical calm, folding his clothes over the chaise. His body, pale and slender, looked fragile. John knew it was not.

“Lubricant is the first principle,” Silas began, his voice taking on the measured tone he used for explaining a fell stitch. “More than seems rational. It must be a flood. Inside and out. The internal mucosa does not produce its own. You are lubricating a colon, not a vagina.” He uncapped a bottle, tipped it, and let a thick, clear stream pour over his cleft, down his perineum. It pooled on the towel beneath him. The smell was clean, odorless, clinical.

“The second principle is relaxation. Not just of the sphincter. Of the mind. Of the belly.” He knelt on the towel, then slowly lowered himself onto his hands and knees, presenting himself. He took a deep, diaphragmatic breath, letting his abdomen sag. The pose was one of total offering. “You will start with your fingers. As before. But slower. You are not preparing me for your cock. You are preparing the pathway for your hand. Each finger is a diameter to be accepted.”

John knelt behind him, his heart a thick drum in his chest. He slicked his right hand lavishly, the lube cold and slick. He placed his left hand firmly on the small of Silas’s back, a point of anchor. “I’m starting.”

He began with his index finger, pressing against the pucker, which was already softened from their nightly activities. It yielded with a soft, wet pop. Heat engulfed him. He worked it in slowly, to the knuckle, then out. In and out, a gentle piston. He added his middle finger alongside it. The stretch was visible now, a slight blooming. Silas moaned, low and encouraging, pushing back.

“Scissor them gently,” Silas breathed, his forehead resting on his folded arms. “Stretch the ring. Not forcefully. Let the muscle warm up and decide to open.”

John did, feeling the incredible, intimate resistance give way millimeter by millimeter. He added a third finger, his ring finger. His own cock was painfully hard, trapped in his trousers, but this was separate. This was work. The three fingers filled his hand; inside Silas, they felt massive. He could feel the tight, gripping ring of muscle just inside, and beyond it, a shocking, silken heat.

“Now the thumb,” Silas instructed, his voice strained. “Tuck it. Make a duck’s beak. Your hand must become as narrow as possible for entry.”

John withdrew, lubed again, and formed his hand into a tapered point, fingers together, thumb tucked tight against his palm. He pressed the smoothed knuckles of his index and middle finger against Silas’s hole. The resistance was profound. This was not a cock, not a toy. It was the widest part of his hand.

“Breathe with me,” Silas panted. “Push on my exhale.”

John felt the shuddering exhale leave Silas’s body. He pushed steadily, not with his arm, but from his shoulder, a constant, unyielding pressure. The outer sphincter stretched, dilated. For a heart-stopping moment, it seemed impossible. Then, with a guttural, granting sound from Silas, the knuckles slipped through.

“Fuck,” John whispered, awestruck. His hand was inside to the mid-knuckles. The heat was otherworldly, a wet, clutching embrace that made his fingers feel acutely, individually alive. He could feel the inner sphincter, a tighter, deeper ring, hugging his narrowing wrist.

“Now,” Silas gasped, sweat beading on his spine. “The hardest part. The widest. The base of the thumb. Go slow. Let me breathe through it.”

John pushed again. The stretch at the opening was obscene. Silas’s hole was distended around John’s wrist, a tight, pink ring against his pale skin, glistening with lube. John watched, mesmerized and a little terrified, as his own flesh disappeared into another man’s body. He felt the second ring of muscle fight, then relent. His hand slid in up to the wrist with a final, wet suck.

They both froze.

John’s entire world narrowed to his buried right arm. He was in up to his wrist. The feeling was incomprehensible. Enveloping, pulsating heat. A gentle, rhythmic pressure from deep within Silas’s gut. He could feel the flutter of Silas’s heartbeat around him, or maybe it was his own pulse thrumming in his trapped hand.

“Oh god,” Silas sobbed, the sound ripped from him. “That’s it. You’re in. You’re fully in.”

John’s thoughts were a static hum. This was intimacy rewritten. He was literally inside Silas, fused to him. There was no hiding, no performance. He felt the raw, animal truth of the man’s need in the clinging, desperate heat of his colon. It was humbling. It was power and surrender inextricably linked.

“Can you feel me?” Silas whispered, trembling.

“Yes.” John’s voice was rough. He flexed his fingers slightly, a gentle kneading motion inside. Silas cried out, his back arching. “I can feel everything. You’re so fucking hot inside. So tight, even now.”

“Move,” Silas begged. “Please. Just a little.”

John began to withdraw, until just his knuckles caught at the inner ring, then pushed back in. A slow, shallow fuck. The sounds were brutally wet, squelching echoes in the quiet room. Each movement made Silas jerk and moan. John’s left hand rubbed circles on Silas’s heaving back.

“You’re taking it so well,” John murmured, a primal praise he didn’t know he possessed. “Your cunt is sucking my hand in. It’s so greedy.”

The filthy word, in this context, shattered Silas. He came violently, his cock jerking untouched, splashing the towel beneath him with thin, clear fluid. The convulsions of his climax were a vice around John’s buried hand, a series of intense, rhythmic milking pulls.

It triggered something feral in John. The careful student vanished. He fucked his hand into Silas with deeper, more demanding strokes, spurred on by the clenching waves. He wanted to own this depth, to claim this extreme intimacy.

“You like that, you fucking whore?” John growled, the words coming from a dark, possessive place. “You like being split open on my fist?”

“Yes! God, yes!” Silas shrieked, his body pliant and wrecked. “It’s all I need! It’s everything!”

John pressed deeper, curving his fingers upward, seeking. He found a subtle, softer spot and pressed. Silas screamed, a sound of pure, unadulterated ecstasy. His body went rigid, then boneless.

John slowly, carefully, withdrew his hand. It emerged with a soft, sucking pop. Silas’s hole gaped, pulsing openly, a vivid, wet, and utterly used oval. He collapsed onto his side, breathing in ragged, sobbing gulps. John looked at his own hand, reddened, slick, smelling profoundly of internal salt and clean lube. He felt like a god. He felt like a servant.

He gathered Silas into his arms, ignoring the mess. Silas clung to him, shaking, murmuring incoherent thanks against his neck. John held him, staring at the opposite wall where their reflection was a blurred smear in the ornate mirror. The garment he was sewing himself into was unlike any he’d ever imagined. It was raw, it was seamless, and it was being stitched from the inside out.

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