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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 4: Fistfuls of Fun

The click of the shop lock echoed like a full stop. In the heavy silence of the west room, John stood trembling, the scent of their shared exertion thick in the air, the cooling spend tacky on his stomach and thighs. Silas returned to the room, his eyes, black and depthless, swept over John’s nakedness, the vulnerability, the raw material of him.

Wordlessly, Silas crossed the space. He placed both hands on John’s broad, hairy chest and pushed.

John went easily, his legs buckling, landing on the plush velvet of the chaise longue with a soft whump. He looked up, dazed. Silas sank to his knees on the rich Persian rug, his movements reverent. He didn’t speak. He simply looked, his gaze travelling the length of John’s body before settling on his cock, which lay against his thigh, still half-hard and gleaming.

Silas leaned in. He didn’t take it in his mouth immediately. Instead, he nosed along the thick shaft, inhaling deeply. “The smell of you,” he murmured, his voice a ragged scrape. “Salt, skin, another man’s spend. It’s perfect.” He pressed his lips to the base, a soft kiss amidst the dark curls. Then another, higher up. He licked a long, slow stripe from root to tip, collecting the mixed wetness there.

John groaned, his head falling back against the armrest, his body going liquid. This was different. With Karen, with the fumbling ghosts of past women, his cock had been a tool, a thing to be used and put away. This worship was something else entirely. Silas treated it like a relic.

He took the heavy ballsac in one elegant hand, lifting it, weighing it. He kissed each orb through the loose skin, his tongue flicking out to trace the seam. He engulfed one, then the other, sucking gently, nursing at them until John was panting, his hips giving tiny, involuntary jerks.

“Fuck, Silas…”

“Yes,” Silas breathed against his skin. Finally, he took the head of John’s cock into his mouth. Not a suck, but a holding. He nursed at it, his tongue swirling around the corona, lapping at the slit. He worked his lips down an inch, then retreated, making a slick, filthy noise. He did it again, and again, until John was fully hard and throbbing, the veins standing out. Silas released him with a pop, looking up, his glasses slightly fogged. “You taste divine.”

“Your turn,” John rasped, the command feeling natural in his mouth. “Sit on my face. I need to taste you.”

Silas didn’t need telling twice. He stood, his fingers flying over his own buttons with a tailor’s speed. Waistcoat, shirt, trousers, underwear—they pooled on the floor in a heap of fine fabric. He climbed onto the chaise, knees straddling John’s shoulders, and lowered himself.

John’s view was obscene and beautiful. Silas’s hole, pink and puffy from the afternoon’s attention, was right there, presented to him. It glistened faintly. He could smell him—a clean, musky scent, utterly male. John’s hands came up to grip Silas’s slender thighs, and he pulled him down the last inch.

He didn’t start with his tongue inside. He nuzzled the cleft of his arse, kissing the perineum, licking behind his balls. He breathed him in, this intimate scent that was now becoming a craving. Then he flattened his tongue and gave one long, broad lick from Silas’s taint all the way up to the top of his cleft.

Silas cried out, a sharp, shocked sound that dissolved into a moan. His body shuddered.

John dove in. He ate Silas out with a hungry, sensual fervour he didn’t know he possessed. He lapped at the furl of muscle, teasing it open with the tip of his tongue before spearing inside. He fucked him with his tongue, shallow and deep, making wet, sloppy sounds that filled the quiet room. He suckled at the puffy, well-developed lips, taking the whole area into his mouth, using his stubble to rasp against the tender skin.

“Oh, god, John… just like that,” Silas whimpered, his hands finding John’s cock again. He stroked him in time with John’s licks, his grip slippery with spit and pre-come. The symphony of sounds was filthy: the wet slap of John’s tongue, Silas’s ragged pleas, the slick friction of his fist on John’s shaft.

This went on for a long, blissful time. They lost themselves in the simple, profound feedback loop of pleasure given and received. This was their favourite sexual situation—no performance, no client, just mutual, greedy satiation.

Eventually, Silas, trembling, shifted. “I need you inside me,” he panted. “Now.”

He moved back, aligning himself. He reached behind, took John’s thick cock in his hand, and guided it to his hole. Still slick from John’s mouth, it yielded beautifully. Silas sank down in one slow, inexorable slide.

John saw stars. The heat, the tight, clutching squeeze was overwhelming. “Christ, you’re so tight,” he grunted.

Silas rode him with a slow, deep rhythm, rising up until just the head remained inside, then sinking back down, taking every inch. He leaned forward, bracing his hands on John’s chest, his silver hair falling around his face. John could feel every internal ripple, every clench. He gripped Silas’s hips, helping to drive him down harder, faster.

“Feel that,” Silas gasped. “Feel how deep you are. You fill me so completely.”

The pace became punishing, instinctive. The chaise groaned beneath them. John could feel his orgasm coiling, a white-hot spring in his gut. Silas’s cock, trapped between their bodies, leaked profusely.

“I’m gonna come,” John warned, his voice raw.

“With me,” Silas demanded. “Look at me. Come with me.”

Their eyes locked. John thrust up one final, devastating time as Silas slammed down. Silas’s body went rigid, a silent scream on his lips as his cock pulsed, spilling hot stripes across John’s stomach. The intense clenching of his hole around John’s length was the trigger. John cried out, his back arching off the chaise as he emptied himself deep inside, wave after wave of blinding release.

They collapsed together in a sweaty, spent heap, John still buried inside him. For minutes, there was only the sound of their struggling breaths slowing. A profound ease settled over them. John’s hand found Silas’s back, stroking it softly. This, too, was new. This comfort in the aftermath.

Eventually, they separated, wincing at the mess. Silas fetched a warm, damp towel from the hidden sink and cleaned them both with a tenderness that made John’s chest ache. They dressed in silence, the simple acts of buttoning a shirt or pulling on trousers feeling like rituals of re-entry into the world.

In the back room, Silas assembled a lunch of leftover bread, cold meats, and mustard. They ate without ceremony.

“Back to it,” Silas said finally, brushing crumbs from his waistcoat.

The afternoon was a study in focused calm. John worked on basting the sleeve of a jacket, his hands steady, his mind quiet and full. Silas drafted a complex pattern on thick paper, his concentration absolute. The shop was filled with the peaceful sounds of their shared craft.

At half past five, Silas put down his shears. “That’s enough.”

“I could keep going,” John said, not looking up from his stitches.

“Your body needs to absorb the new motor skills. The neural pathways need to cement without fatigue. Trust me. We stop while we’re ahead.”

They closed the shop fully, pulling the heavy security grille down with a final rattle. Up in the flat, Silas mixed gin martinis, shockingly cold and clear. He cooked while John drank his: a simple pasta with garlic, chilli, and a staggering amount of Parmesan.

After they’d washed up, they settled in the living room with a second drink. The easy silence returned, but John sensed a tension in Silas, a hesitation.

“Something on your mind?” John asked.

Silas swirled the liquid in his glass. “There’s something… a need of mine. I feel I should tell you.”

“Okay.”

“It’s about my hole,” Silas said, the clinical word stark in the cozy room. “It requires… a lot of attention. Not just regular fucking. A significant amount of stretching. A feeling of being profoundly filled. Most nights, I need that.”

John’s curiosity prickled. “What does that mean, exactly?”

Silas met his gaze. “Fisting.”

The word hung in the air. It was not one from John’s lexicon. He’d seen things online, fleeting, confusing images. “Right.”

“I have a toy. A very good one. I’m perfectly content with it. I don’t want you to feel obligated in any way. But I also don’t wish to exclude you, if it’s something you might… find interesting.”

John felt a strange thrill, a curiosity that overrode any kneejerk squeamishness. This was Silas, who had rewired his understanding of pleasure. “I’d like to see,” he said. “I mean, if you’re showing me… I’d like to try. If that’s alright.”

A visible relief softened Silas’s features. “That’s perfectly acceptable.”

He led John to the bedroom. From a lacquered chest, he withdrew a series of silicone shapes, graduating in size from a modest plug to a terrifying, hand-like form. He laid them on the bed.

“It’s about patience,” Silas explained, his voice slipping into a teacher’s tone. “Lubricant is paramount. More than you think could ever be necessary. It’s about listening to the body’s signals, not forcing. It’s about the stretch, the fullness, the surrender.”

He had John sit in an armchair. Then, with a performer’s grace, Silas began. He poured a bottle of clear, thick lube over his fingers, letting it drip onto his arsehole. The sticky, slick sounds were immediate. He worked two, then three fingers into himself with practiced ease, his head falling back, a soft sigh escaping him.

“Watch how I open myself,” he whispered.

John watched, mesmerized. Silas used the toys, starting with the smallest. He pressed the silicone bulb against his loosened hole and, with a slow, controlled breath, let it slide in. He moaned, low and deep. He moved to the next size, repeating the process. Each time, his hole gaped slightly more after the toy was removed, shiny and inviting.

The room smelled of sex and silicone. Silas’s movements were hypnotic, a slow-motion dance of self-impalement. He was on the largest toy now, the one shaped like a clenched fist. He lubed it obscenely, coating every ridge.

“This is my favourite,” he breathed. He positioned himself over it, on his knees, and began to lower himself. It was a slow, incredible descent. John could see the silicone stretching him wide, disappearing inside him inch by impossible inch. Silas’s face was a mask of ecstatic concentration.

A guttural moan tore from John’s throat, unbidden.

Silas paused, the toy halfway inside him. He looked over his shoulder, his eyes black pools. “Would you like to take over?”

John was across the room before the question finished. He knelt behind Silas, his hands replacing Silas’s on the toy. He pushed gently, feeling the incredible resistance, the hot, silken tightness yielding to the relentless pressure. With a final, wet pop, the entire fist slipped in, up to the wrist.

“Oh my god,” John breathed. He was inside Silas in a way that defied belief. He could feel the heat, the cling of internal muscles around the foreign shape. He began to move it, a slow fuck in and out. The sight was brutally obscene. Silas’s hole was a stretched, pink ring around the thick silicone wrist, glistening and slack.

“Your hand,” Silas begged, his voice shattered. “I want your real hand. Please, John.”

John withdrew the toy. His own hand, slicked with more lube, looked huge. He pressed his fingers together, forming a beak. He pressed against that utterly used, open hole. It gave way with shocking ease, swallowing his fingers, then his knuckles. The heat was incredible, a wet, gripping furnace. He pushed slowly, carefully, listening to Silas’s hitched breaths. He felt the inner muscles relax, accept, welcome. His entire hand, up to the wrist, slid inside.

Silas screamed, a raw, unfiltered sound of pleasure. John was elbow-deep in him, fused to him. He could feel the internal architecture of the man, the pulse and the heat. It was the most intimate thing he had ever experienced.

“Fuck me,” Silas sobbed. “Fuck my sloppy cunt with your cock, too. Fill me completely.”

John withdrew his hand, his mind reeling. He positioned his cock at that ruined, beautiful opening. It slid in alongside his fingers with no resistance, buried in an incredible, wet heat that was now cavernous. He began to move, fucking him with his cock while his hand remained inside, moving in tandem. The squelching, slapping noises were animalistic. Silas was babbling, incoherent with bliss, pushing back onto both invasions.

John lost all sense of time, of self. He was a machine of giving, of filling. The stretch of Silas around his combined girth was a tangible, tight sensation even within the looseness. His own orgasm built from a deep, primal place. When it came, it was a silent, seizing thing, draining him utterly as he pumped his seed into that willing, stretched channel. Silas came untouched, his body clamping in rhythmic spasms around John’s embedded limbs, a dry, shuddery climax of pure sensation.

They collapsed sideways on the bed, still joined in the most profound way. John carefully, slowly, withdrew. Silas’s hole gaped, pulsating, a wet, well-used flower. They lay in a heap of limp limbs, mindless, spent, and closer than either had thought possible. John was swimming in a profound emptiness, his entire nervous system humming with the aftershock of what they’d just done. He turned his head on the damp sheets, looking at the ruin of Silas beside him. Silas’s eyes were closed, his breathing still erratic, his body loose and conquered.

Then John remembered. He remembered the conversation from earlier, over the gin cocktails after Silas had explained the rhythm of his world—the giving, the receiving, the need to be anchored afterwards. The instruction had been clear and clinical: after such vulnerability, I require this.

Without thinking, his body moved before his mind could second-guess it. He shifted on the bed, sticky with lube and sweat, and gathered Silas into the cradle of his arms. Silas was pliant, his narrow frame folding easily against John’s broader chest. John pulled him close, wrapping limbs around him, enclosing him completely. One hand came up to cup the back of Silas’s head, pressing his face into the hollow of his shoulder. He blindly grabbed a blanket from the foot of the bed and pulled it up and over them both, creating a warm, dark cocoon.

Silas trembled once, a full-body shudder that was not a chill, but a release of tension so deep it seemed to emanate from his bones. Then he melted. A long, slow sigh feathered against John’s neck. John said nothing. He just held him, his own hand beginning a slow, automatic stroke up and down the knobs of Silas’s spine. He felt the frantic pulse at Silas’s throat gradually begin to slow and synchronize with his own.

John’s mind whirled in the quiet dark behind his eyelids. He’d never held someone like this after sex. With Karen, it had been a brief, obligatory spoon before rolling apart to sleep. This was different. The acts themselves had been shocking in their intensity, a language of flesh and filth that bypassed all his old understanding. There were no mind games here, no guessing. Silas had simply told him what he needed—to be fucked, to be filled, to be held. The communication was as direct and unembellished as a cutting instruction. All the work was in the doing, the physical execution, and John, whose body had always been his most reliable instrument, had discovered a profound aptitude for it. He liked the clarity. He loved the weight of Silas’s trust.

As their breathing evened out, John felt the inevitable awareness of his own size, the potential for his embrace to become an entrapment. The internal reflex to give space, to retreat, kicked in. He began to loosen his hold, to shift his weight back from Silas.

A hand, slender but surprisingly strong, clamped over his wrist. Silas’s grip was desperate.

John stilled. His hand resumed its stroking, tracing the ridge of Silas’s exposed shoulder blade, then down the sharp dip of his flank. He felt the fine tremors subsiding beneath his palm. The air under the duvet was warm and smelled of sex and safety.

“You alright?” John whispered, his voice rough from disuse.

Silas turned his head slightly. John could feel the shift of his nose against his skin. He could just make out the glint of his eyes in the near-dark. “More than,” Silas breathed, his voice thin but sure. He pressed back against John, fitting himself more firmly into the curve of John’s body. “Stay. If you’re comfortable.”

John smiled into the darkness. He bent his head and pressed his lips to Silas’s silvered temple. The kiss was dry and chaste, a punctuation mark. “I’m more than comfortable,” he murmured.

As he spoke, he felt the undeniable, renewed thickening of his own cock. It stirred, heavy and full, coming back to life with a swiftness that startled him. It pressed insistently against the small of Silas’s back, a blatant, heated presence.

Silas felt it. He let out a contented groan, a sound of pure, lazy delight. Without a word, he twisted in John’s arms. He slid down, his body a graceful eel under the blanket. The blanket shifted and rose as he moved, a tent of darkly woven fabric, and then John felt the warm, seeking pressure of Silas’s hands and then his mouth.

Silas’s lips encircled the head of his cock, not taking him deep, but holding him. He suckled softly, his tongue swirling in a slow, dedicated pattern. He made a low, humming sound in his throat that vibrated through John’s shaft. It wasn’t a blowjob aimed at an end; it was communion. Silas nursed at him, his mouth a wet, worshipping vessel, pausing to lap at the slit, to nuzzle the veins, to simply breathe the musky scent.

John had never known this. His cock had been sucked before, but never adored. Silas treated it with a curious, reverent attention, as if studying its texture, its weight, its response. The sounds were obscenely intimate: the soft, wet pulls of Silas’s mouth, John’s choked sighs, the rustle of bedding. John’s hand found the top of Silas’s head under the duvet, his fingers threading through the fine, soft hair, not guiding, just connecting.

“Christ, your mouth,” John gasped.

Silas responded by sliding lower. He took John’s heavy sac into his mouth, one ball then the other, rolling them with his tongue. He suckled gently, then released them with a wet pop. He slathered them with saliva, his tongue painting the loose, sensitive skin, nibbling at the seam. He lavished attention there until John was squirming, his hips canting upward.

Then Silas surfaced. He pushed the duvet back, his hair mussed, his lips slick and swollen. “Turn over,” he said, his voice a husky command. “On your stomach.”

John’s brain stuttered. The command was clear, but it cut against a lifetime of hetero scripting. To present himself like that… vulnerability of a different, deeper kind. He hesitated. But the memory of Silas’s fingers inside him that first day flashed—the surprising shock of it, the lack of revulsion. And he’d just seen, had just participated in, the ecstasy Silas derived from the same act. Curiosity, sharper than fear, won.

“Okay,” he said, his voice tight.

He rolled onto his stomach, the sheets cool against his flushed skin. He felt absurdly exposed, his broad back, his hairy arse cheeks parted by his position. He buried his face in the crook of his arm, his heart hammering.

He heard Silas move, felt the dip of the mattress as he repositioned himself. Then, nothing but the sound of their breathing. Anticipation was a live wire under his skin.

The first touch wasn’t his tongue. It was Silas’s hands, kneading the flesh of his buttocks, spreading them gently apart. A thumb traced the outer rim, a feather-light pass that made John jolt.

“Just breathe,” Silas murmured, his voice close. “Feel it.”

Then came the warmth of his breath, a soft puff against his hole. John shuddered. The first touch of Silas’s tongue was a flat, broad swipe from his taint all the way up to the top of his cleft. It was shocking, wet, and startlingly pleasurable. A choked sound escaped John’s throat.

Silas didn’t rush. He licked him like a man savoring a complex dish. He traced circles around the pucker, teased the outer ring with the very tip of his tongue, kissed it. He spread John wider and explored the entire area—the perineum, the sensitive skin just behind his balls, the tight furled star itself. Each movement was deliberate, designed to map and awaken. He was teaching John’s body a new alphabet of sensation.

John was dissolving. The hyper-awareness was dizzying. He felt every minute shift of pressure, every wet stripe, the scratch of Silas’s stubble against his inner thighs. Pleasure, clean and bright, was building from a place he’d never considered a source. He was moaning openly now, low, animal sounds he didn’t recognize as his own.

Silas hummed against him, the vibration shooting straight up John’s spine. He began to focus, his tongue becoming more pointed, more insistent. He pressed the tip against John’s hole, flicking rapidly. He pushed, just a little, and John’s body yielded.

“Fuck,” John groaned into the mattress, his fists clenching the sheets.

Silas speared his tongue inside. It was a shallow invasion, but profound. He fucked him with it, in and out, in a wet, sloppy rhythm. The sounds were filthy, lewd, and undeniable. He was opening him up, tenderizing him with saliva and relentless attention. John felt his own muscles, tight and unfamiliar, beginning to relax, to welcome the intrusion.

The sensation crested from strange to imperative. He needed more. This tongue-fucking was a tantalizing preview, a maddening itch he needed properly scratched.

“Please,” John begged, his voice raw and broken. “Silas… please fuck me. I need your cock. I need it now.”

Silas pulled back, panting. John heard the fumble for lube, the slick squirt, the wet sounds of Silas coating himself. He felt the blunt, cool pressure of Silas’s smaller cockhead against his hole, now soft and slick and welcoming from the diligent tongue-work.

“Slowly,” Silas whispered, more to himself than to John. He pressed. There was a burn, a stretching sensation so foreign it made John gasp. But it wasn’t pain; it was a fierce, full pressure. Silas was smaller than him, a fact for which John was profoundly grateful in that moment, but he was still a solid, invading presence.

An inch slipped inside. John hissed. Silas held still, letting John’s body adjust, his hands soothing on John’s flanks. Then another inch. And another. The feeling of being filled, of being penetrated, bloomed in John’s consciousness. It was overwhelming, a total subversion of everything he’d known. As Silas seated himself fully, John felt a new, internal pressure against his front wall, a spot that seemed to hum with electric potential.

Silas began to move, a shallow, careful rocking. He adjusted his angle slightly, and on the next thrust, his cockhead brushed that spot again.

“Oh my god!” John cried out, his whole body seizing. White sparks exploded behind his eyes. It was a pleasure so acute it bordered on pain, a deep, prostate-centric thunderclap that rewired his brain.

“There it is,” Silas coaxed, his voice tight with his own effort. He set a rhythm now, each thrust aimed with precision. Every pass over that magical spot made John sob. The noises in the room were a symphony of raw need: the wet slap of skin, the creak of the bed, John’s shameless, guttural moans, Silas’s sharp, controlled breaths.

“I can feel it… inside you… so tight,” Silas grunted. His control was fraying. His thrusts became shorter, harder, deeper. His fingers dug into John’s hips. “Gonna come… gonna fill this perfect hole.”

John was beyond words, lost in the piston-fire stimulation of his prostate, the incredible fullness. He felt Silas stiffen, then the hot, internal pulse as Silas emptied himself with a ragged cry, spilling deep inside.

Silas collapsed on top of him for a moment, then slid out. He turned John over with surprising strength. John’s cock, untouched and weeping, stood rigid against his belly. Silas, still wet with his own release, straddled him. He reached behind, guided John’s thick length into his own well-used, loose channel, and sank down in one smooth motion.

He rode John with a slow, grinding exhaustion, their mutual sweat-slick bodies sliding together. John’s hands gripped Silas’s bony hips, watching himself disappear into the man who had just claimed him. The visual, the slick heat, the spent intimacy of it, pushed him over. He came with a silent, seizing intensity, pumping up into Silas’s depths until he was utterly empty.

Silas slid off, and they lay side-by-side, two wrecked vessels on a shore of rumpled linen.

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