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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 2: John's first fitting session descends into raw debauchery when the client demands to 'inspect the merchandise' up close, forcing John to his knees as Blackwood watches approvingly.

The flat felt smaller that night. The walls seemed to press in, stained with the ghost of every silent argument. Karen had used the cash for the electric and ordered a Chinese. They ate it off their laps in front of the telly, the grease from the sweet and sour sauce gleaming under the flickering light of a property show.

“This is nice,” she said, not looking at him, chasing a piece of chicken with her chopsticks.

“Yeah,” John agreed, his voice hollow. His body still thrummed with the memory of the chaise, of Silas’s tight, clinging heat. The taste of him was a phantom on John’s tongue. He felt like a smuggler, carrying contraband warmth into this chilled, familiar space.

“So this fabric bloke,” Karen said during an ad break. “It’s regular?”

“Looks like it,” John said, focusing on a noodle. “Few days a week. Cash in hand.”

“Good.” She nodded, a decisive little movement. That was the end of the interrogation. The money had validated the lie. The relief was a sour taste in his mouth.

He showered before bed, scrubbing hard, as if he could erase the feeling of being known so intimately by a stranger. But under the spray, his hand drifted, remembering the grip, the depth. He came quickly, silently, biting his fist to stop the groan, his mind a riot of images—black eyes, silver hair, pink, puffy flesh. Guilt followed instantly, cold and shrivelling.

The next morning, he shaved with meticulous care. He studied himself in the bathroom mirror. The bloke looking back was the same, but the eyes held a new secret. A furtive energy. He dressed in plain dark jeans and a black t-shirt, as instructed.

The bell’s weak jingle was now a familiar herald. Silas was at the cutting table, but today he was not alone.

A man stood by the bolts of grey flannel, his back to the door. He was tall, almost as tall as John, but lean where John was broad, encased in a suit so understated it screamed expense. His hair was steel-grey, cut with sharp precision.

“Ah, John. Excellent,” Silas said, his voice smooth as poured oil. “Our appointment is at noon. This is Mr. Everard.”

The man turned. He was perhaps in his late fifties, with a face that was all angles and calculated calm. His eyes, a pale, watery blue, swept over John with the detached assessment of a man reviewing a ledger. There was no warmth, only a deep, quiet intensity.

“John,” Mr. Everard said. His voice was dry, quiet.

“Sir,” John replied, the word sticking in his throat.

“We’ll be using the east room,” Silas said, gathering a garment bag and a small, polished case. “John, with me.”

The east room was the second private fitting room. Silas had prepared it. The chaise had been straightened. A single, high-backed chair had been placed opposite the triple mirror. On a small side table sat a crystal glass and a decanter of amber liquid.

“The dynamic is particular,” Silas murmured, hanging the garment bag and opening his case. Inside, nestled in folds of black silk, were items of clothing. Not suits. “Mr. Everard is a connoisseur of form. Of contrast. He enjoys the juxtaposition of the refined and the… elemental. You are the elemental. Your role is to be still. To be observed. To allow the clothing to speak, and then to allow what is beneath the clothing to speak louder. Do not speak unless he asks you a direct question. Do not initiate touch. Understood?”

John’s mouth was dry. He nodded.

“Good. We begin with the base layer. This.”

From the case, Silas drew out a pair of briefs. But they were not cotton. They were a deep burgundy silk, so fine they seemed liquid. And they were lace. A delicate, open pattern.

John stared. “You’re kidding.”

“I am not.” Silas’s tone brooked no argument. “They are constructed for support. Put them on.”

Feeling a fool, John stripped, his skin prickling under the cool, silent gaze of the mirrors. He stepped into the briefs. The silk was shockingly soft, cold against his skin. The lace panel at the front stretched over his limp cock and balls, a stark, dark shadow behind the intricate pattern. They cut high on his hips, cupping his arse, which felt exposed and strangely presented.

Silas adjusted the waistband with a tweak. “Now. The trousers.”

They were part of a suit, fine charcoal wool. But John wore only the trousers. Silas buttoned the fly, the expensive fabric sighing as it enclosed him. The wool felt foreign against his bare skin. He was half-dressed, half-doll.

“Stand here,” Silas directed, positioning him on a marked spot on the floor before the mirrors. “Look at your own reflection. Do not look at him when he enters.”

Silas left, closing the door softly. John was alone with the multiplying images of himself. The big, hairy man in suit trousers and lace burgundy briefs. He looked absurd. He looked, he realized with a jolt, profoundly sexual. The contrast was the point. The powerful frame forced into delicate fabric. The secret filth beneath the respectable wool.

The door opened. Mr. Everard entered, followed by Silas. Everard took the high-backed chair, crossing one long leg over the other. Silas stood slightly behind him, a silent attendant.

The room was silent except for the faint rustle of Everard’s sleeve as he reached for the glass of whisky. He took a slow sip, his pale eyes fixed on John.

“Walk,” Everard said. The word was a soft command.

John walked the length of the room, turned, walked back. The wool whispered. He felt the brush of the lace against his thickening cock. He stopped on the mark.

“Turn. Slowly.”

John turned, showing his back, the way the trousers clung to his arse.

“The drape is exceptional, Silas,” Everard remarked, his voice casual, as if discussing the weather. “No pulling across the glutes. Clean.”

“Thank you. The fit through the thigh is key for a form this substantial.”

“Remove the trousers.”

John’s fingers fumbled with the button and zip. He pushed the trousers down, stepping out of them. He was left in only the lace briefs, standing before these two men, his flesh heating under their gaze. His cock was filling out, stretching the delicate silk.

Everard’s eyes didn’t waver. He took another sip. “The next layer.”

Silas moved forward. From the case he produced a harness. Not the harsh leather of a fetish shop, but a harness of supple, black leather straps, elegantly minimalist. He helped John into it. It fitted snugly around his waist and thighs, a central ring sitting flush against the lace, encircling the base of his now fully erect cock, which pressed insistently against the burgundy silk.

“Better,” Everard breathed, leaning forward slightly. “The industrial against the ornamental. Continue.”

Silas next brought out a shirt. A dress shirt of stark white cotton. He helped John into it, leaving it unfastened, so it hung open, framing his hairy chest and the black harness straps. The image in the mirror was dizzying: the formal shirt, the aggressive harness, the lace straining over his erection.

“Exquisite,” Everard murmured. He set his glass down. His hand, long-fingered and elegant, moved to his own lap. John heard the subtle click of a belt buckle. “The final element, Silas.”

From the polished case, Silas drew out one last item. A collar. Wide, black leather, with a single, dull silver ring at the front. He fastened it around John’s neck. It was not tight, but its presence was absolute. A final declaration of ownership, of use.

John’s breath came in short pants. He was on display, transformed into a sculpture of contradicting desires. He watched in the mirror as Mr. Everard, his expression still one of calm appraisal, unzipped his own trousers and freed his cock. It was neat, circumcised, aristocratically pale. He began to stroke himself, his movements slow, measured.

“Come closer,” Everard said.

John took two steps forward, stopping a few feet from the chair. The man’s eyes raked over him, from the collar to the open shirt, down the harness, to the lace-covered cock.

“Silas. The lace is obscuring the view.”

“Of course.”

Silas moved in. With a deliberate slowness, he hooked his fingers into the waistband of the briefs and peeled them down John’s thighs. John’s cock sprang free, jutting up, thick and flushed, through the ring of the harness. The cool air kissed the wetness already beading at the tip.

Everard’s stroking rhythm increased, just slightly. “Magnificent proportion. As you promised.” His pale eyes flicked to the mirror, meeting John’s reflected gaze. “You may touch yourself. Match my rhythm.”

John’s hand wrapped around himself. The feel of his own flesh, warmed by the lace, was electrifying under this observation. He began to jerk his cock, his fist moving in time with Everard’s. The only sounds were their breathing and the soft, slick friction of skin on skin.

“Look at yourself,” Everard commanded, his voice tighter now. “See what we see. A beast trussed in silk and leather. A tool of beautiful function.”

John looked. He saw a man he barely recognized, collared and harnessed, being watched by a powerful stranger who was calmly jerking off. Shame tried to rise, but it was drowned in a flood of dizzying, potent arousal. His hips began to push minutely into his fist.

“He’s responsive,” Everard noted.

“Very,” Silas said from the shadows, his own gaze hot on John’s skin.

“Turn around. Show me how the harness accentuates the glutes.”

John turned, presenting his arse, the black straps cutting into the flesh of his cheeks, framing his hole. He continued to stroke himself, his arm stretched behind him.

“Perfect. Silas, prepare him.”

John heard the click of a cap, the wet sound of lube. Then Silas’s cool, slick fingers were on him, pressing, circling, before one slipped easily inside. John moaned, his forehead dropping against the wall mirror. The penetration was clinical, a preparation, but it sent jolts of pure need through him.

“He’s ready,” Silas said.

“Finish your demonstration.”

Silas’s finger withdrew. John heard the rustle of clothing, the sound of a zip. Then Silas was pressed against his back, his own cock, hard and insistent, nudging at John’s entrance. Silas’s hand wrapped around John’s, guiding his stroking, making it harder, faster.

“Now,” Everard said, his voice a sharp gasp.

In one smooth, brutal thrust, Silas sheathed himself fully inside John. John cried out, the fullness breathtaking, the ache profound. Silas held still, buried deep, his breath hot on John’s neck.

“Watch him,” Silas growled in John’s ear, nodding towards the mirror.

John’s bleary eyes focused. In the reflection, he saw Mr. Everard, his composure finally shattered, his jaw clenched, his hand a blur on his cock as he stared fixedly at the point where Silas’s body joined John’s.

“Move,” Everard choked out.

Silas began to fuck him. Deep, punishing, precise strokes that drove John forward into his own fist with every thrust. It was a machine of pleasure, each part working in sync: Silas’s cock stretching him wide, his own hand working his leaking shaft, Everard’s frantic masturbation providing the frantic, visual metronome. The slap of skin, the grunts, the hissed profanities filled the velvet-draped room.

“God, look at you take it,” Everard moaned, his pace frantic. “You fucking animal. Take it.”

John was unravelling. The sensory overload was total. The submission, the display, the raw physical fucking coalesced into a white-hot point in his spine. “I’m gonna come,” he rasped, a warning, a plea.

“On his harness,” Everard ordered, his voice cracking. “Mark it.”

With a shout that was torn from his guts, John obeyed. Thick, white ropes shot from his cock, splattering across the black leather straps of the harness, dripping onto the fallen lace briefs around his ankles. The convulsions of his orgasm clenched around Silas, who drove into him twice more before stilling with a guttural cry, his own release pumping hotly inside John.

A second later, with a sharp cry, Mr. Everard came, his spend striping the front of his own immaculate trousers in violent pulses.

Silence fell, broken only by the sound of ragged breathing. Silas slowly pulled out. John’s legs wobbled. He stayed leaning against the mirror, spent, marked, the smell of sex and leather thick in the air.

Everard stood, tucking himself away with a weary, satisfied efficiency. He tossed a heavy, sealed envelope onto the side table next to the decanter. His calm had returned, though his face was flushed.

“A satisfactory calibration, Silas,” he said, straightening his cuffs. “The proportions are indeed ideal. I shall be in touch regarding the commission.” His pale eyes swept over John’s ravaged form one last time, a collector noting the condition of an acquired piece. Then he left, the door clicking shut behind him.

John slid down the mirror to sit on the floor, amidst the discarded clothing. Silas fetched a warm, damp towel. He cleaned John with a strange, focused gentleness, wiping the spend from the harness, from his stomach. He unfastened the collar, then the harness, his fingers soft.

“You were extraordinary,” Silas said, kneeling before him. He cupped John’s cheek. “You understood the assignment perfectly.”

John looked up at him, his mind blank, his body a hollowed-out shell. “What was that?”

“That,” Silas said, standing and retrieving the envelope, “is the heart of the business.” He counted out a stack of fifty-pound notes, far thicker than the previous day’s bundle, and pressed them into John’s hand. “A client’s fantasy, impeccably tailored. You are the raw material, John. And you are superlative.”

The money felt heavy. Tainted. Vital.

“He… he came just from watching.”

“Many of them do,” Silas said, helping John to his feet. “The power is in the watching. In the curation. You provide the truth they lack. The animal reality.” He began to gather the clothing, folding the lace briefs with reverence. “Tomorrow, we rest. The day after, we have another appointment. A different… aesthetic.”

John stood there, the heavy notes still in his palm, the smell of the man’s cologne and their combined spend clinging to the air. His skin felt tight, humming, his arse tender and wet. “Right,” he mumbled, the word inadequate for the seismic shift in his reality. “So… what’s next?”

Silas looked at him, a hint of surprise in his dark eyes.“Next? You are welcome to leave. Your job, for today, is quite done.” He gestured to the money in John’s hand. “You’ve earned it. Go home. Rest.”

But John didn’t move. The thought of returning to the silent flat, to Karen’s distant curiosity, felt like stepping off a cliff into a cold sea. Here, in this strange, scented den, he felt… purpose. A terrible, thrilling purpose. He stuffed the cash into his pocket and hovered near the cutting table as Silas methodically put the room to rights.

“You work a lot,” John said, watching the older man’s precise movements.

“It is my life. The shop. The clients.” Silas didn’t look up from smoothing a bolt of mohair.

“Are you… married to it, then?”

A faint smile touched Silas’s thin lips. “Only to my job. It is a demanding spouse, but a faithful one.”

“What do you do besides this?” John asked, leaning against the table. “Got a… I dunno, a book club or something?”

Silas let out a dry chuckle, a rare, unguarded sound. “Nothing so communal. The occasional theatre production. A private view at a gallery. That is all. I enjoy the life the shop brings me. And I’m good at it.”

“Yeah,” John said, his voice low. “You are. I can see that.”

Silas paused his tidying and looked at John, really looked at him. “Are you fishing for something, John?”

“No. Just… making conversation. Killing time, I suppose.” John shrugged, a big, awkward motion. “This life. Does it make you happy?”

Silas considered the question, his gaze turning inward for a moment. “Deeply. It provides a certain… clarity. A structure to desires that are often formless.” He paused, his eyes finding John’s again. “A little lonely at times, but such is life. Loneliness is not always a vacuum. Sometimes it is simply space waiting to be filled.”

John nodded, understanding the shape of that space all too well. His eyes drifted from Silas’s face to the tools of his trade: the shears, the chalk, the rolls of exquisite fabric. “Show me how you do it,” he said suddenly.

“Do what?”

“The cutting. The… making. It’s just cloth, right? But you turn it into something else.” John reached out, his calloused fingers brushing the surface of a length of midnight-blue cashmere. It was softer than anything he’d ever touched.

Silas watched the gesture, an intrigued gleam in his eye. “It is geometry. Anatomy. Illusion.” He picked up a large pair of dressmaker’s shears, their blades sharp enough to slice light. “Precision is everything. A tremor, a miscalculation of a millimetre, and the entire garment is compromised.”

He took a large offcut of sturdy wool melton, a practice piece, and laid it on the cutting table. With a swift, confident motion, he drew a complex pattern onto the fabric with chalk. “Your turn. Cut along the line. Not beside it. On it.”

John took the shears. They were heavier than he expected, perfectly balanced. He lined up the blades, his hands—which had just been gripping his own cock, which had been clenched into fists—now stilled, focusing. He took a breath and cut. The blades hissed through the dense wool, a clean, satisfying sound. He followed the curve of Silas’s chalk line, his large hands surprisingly steady.

Silas watched, silent. When John finished, setting the shears down with a soft click, Silas picked up the cut piece. He examined the edge, holding it up to the light. He said nothing for a long moment.

“Again,” he said, his voice different. Softer. He handed John another offcut, this time with a more intricate, curving pattern.

John cut. And again. Each time, his movements grew more assured, his focus narrowing to the line, the shear of the blades, the fall of the cloth. The physicality of it, the simple, measurable achievement, was a balm. He wasn’t failing. He was making.

“Well,” Silas said finally, after the fourth perfect cut. A genuine smile, warm and uncalculated, touched his eyes. “That is a surprise. You have a natural feel for it. A steady hand.”

A flush of pride warmed John’s chest, cleaner than any arousal. “Just following instructions.”

“Many cannot.” Silas gestured toward the back. “Come. A break is in order. You’ve earned more than just money today.”

They sat in the small lounge room, in the worn leather armchairs. Silas poured two glasses of water from the carafe in the mini-fridge. The quiet felt comfortable, shared.

“I like pleasing you,” John said, the words out before he could stop them. He looked into his glass. “Not just… the other stuff. This. The cutting. Getting it right. I’m grateful for… for the opportunity. All of it.”

Silas swirled his water, watching him. “You’re a man of unexpected depth, John. It’s intriguing.” He took a slow sip. “But I find myself curious. Is there another reason you’re hanging around? The money is in your pocket. The day’s performance is concluded.”

John’s throat tightened. The image, seared into his mind from the day before, rose unbidden: Silas bent over the chair, that shocking, pink, beautiful hole presented to him. The taste, the smell, the desperate, hungry sounds he’d drawn from the older man. His cock, which had been soft, began to thicken against his thigh.

He looked up, meeting Silas’s penetrating gaze. His voice was a low, rough scrape. “I can’t stop thinking about your hole, Silas. That beautiful, fucked hole of yours. I dreamt about it.”

Silas didn’t blink. His expression didn’t change, but a dark heat flooded his eyes. Without a word, he stood. He turned his back to John, facing the wall of fabric samples. His hands went to his waist, undoing his immaculate trousers. He pushed them, along with his underwear, down to his knees. Then he bent forward, placing his palms flat against the wall, presenting himself fully.

The sight was just as devastating as the first time. Perhaps more so, because now John knew the texture, the taste. The pale cheeks parted, the centre a glistening, puffy rosette, used and inviting, a dark pink flower against the white skin.

John was on his knees in an instant. He didn’t hesitate. He buried his face between Silas’s arse cheeks with a groan that was pure hunger.

He started broad, lavishing the entire area with his thick, wet tongue. Long, flat strokes from his taint up to the small of his back, soaking the skin. Silas shuddered, a low sound escaping him. Then John focused. He circled the wrinkled aperture with the blunt tip of his tongue, teasing, applying pressure without penetrating.

“Christ, John…” Silas breathed, pushing back.

John obeyed the unspoken command. He pointed his tongue and pressed inside. The ring of muscle yielded easily, welcoming him into the incredible, tight heat. He fucked into him with his tongue, shallow at first, then deeper, spearing as far as he could go. He curled it, searching, and was rewarded with a guttural moan from above. He alternated techniques: deep, probing thrusts, then fluttering, rapid flicks right at the sensitised rim. He sucked on the puffy flesh itself, drawing it into his mouth, grazing it gently with his teeth, making Silas jerk and curse.

John lost himself in the act. It was not subservience; it was a kind of worship, a giving of pleasure that fed his own in turn. He was achingly hard. One hand gripped Silas’s hip, the other, moving almost of its own volition, dropped to his own jeans. He undid his fly, freeing his own cock. Then his slick fingers found their way back, past his balls, to his own hole.

He probed himself, his finger slipping in easily, still loose and slick from Silas’s cum earlier. The dual sensation was mind-bending: his thick tongue plunging into Silas, his own finger working into his tender passage. He grunted into the older man’s arse, the vibrations wringing another broken cry from Silas.

“John… fuck… your tongue…” Silas was panting, sweating, his knuckles white against the wall. “Please… I need more. I need your cock. Fuck me. Please, fuck me now.”

John pulled back, his mouth and chin soaked. He stood on shaky legs, his own need a painful throb. He didn’t bother removing his clothes fully, just shoved his jeans down around his thighs. He spat into his palm, slicking himself generously, his own saliva mixing with Silas’s taste. He positioned his thick head at that glistening, well-prepared entrance.

He pushed in slowly, agonisingly slowly, savouring every millimetre of yielding, tight heat. Silas groaned, long and low, his body opening, accepting him utterly. When John was fully sheathed, he stopped, leaning forward, blanketing Silas’s back with his chest. He kissed the side of Silas’s neck, his jaw, salty with sweat. He turned Silas’s head and found his mouth, kissing him deeply, sharing the taste of himself.

“So good,” John slurred against his lips. “You feel so fucking good.”

He began to move. Not a frantic pounding, but a slow, deep, sensual roll of his hips. Each withdrawal was a tease, each penetration a profound homecoming. He fucked him with a purposeful, measured rhythm, one hand braced on the wall, the other roaming Silas’s chest, pinching a nipple, stroking his flank.

Silas was incoherent, babbling praise and filth into the fabric samples. “Yes… like that… so deep, you fill me so perfectly… God, your cock…”

John kissed him again, sloppy and wet, their teeth clashing, their tongues duelling. Saliva trailed from their mouths. The pace built gradually, naturally, the wet sounds of their joining filling the small room. It was an intense, consuming connection, raw but not brutal, intimate beyond anything John had known.

When John felt his climax coiling, a tight spring in his gut, he reached around and took Silas’s leaking cock in his fist. A few strokes were all it took. Silas came with a shattered cry, his seed spurting over John’s hand, his channel clamping down in rhythmic pulses. The sensation tipped John over the edge. He drove in one last time, hilting himself, and emptied deep inside with a guttural roar, his body shuddering against Silas’s.

They slumped against the wall, a tangle of spent limbs and damp clothing, breathing in ragged unison. Slowly, John softened and slipped out. He righted his own clothes with clumsy hands before tenderly pulling up Silas’s trousers, fastening them for him.

Silas turned, his face flushed, his silver hair tousled, his glasses slightly askew. He looked dazed, wrecked, beautiful. He reached out a trembling hand and touched John’s cheek. “That was…”

“Yeah,” John finished, his voice hoarse.

After a moment, Silas glanced at the old railway clock on the wall. “Do you have plans this evening?” he asked, his voice regaining some of its usual composure, though his eyes remained soft.

John thought of the flat, the ready meal, the television’s glow on Karen’s distracted face. The crushing, lonely normalcy of it. “No,” he said. “No plans.”

A genuine, warm smile touched Silas’s lips, the kind that reached his eyes and transformed his sharp features. “Good. I have tickets for a play at the Almeida. And there’s a small French place in Islington I’ve been wanting to try. I would be… very pleased if you would accompany me.”

John looked at this man, this strange, elegant, complicated man who had pulled him into a world of velvet and filth and unexpected precision. He felt the thick envelope of cash in his pocket, the pleasant ache in his body, the sharp, clean memory of making a perfect cut. He couldn’t think of a single better way to spend his time.

“Yeah,” John said, a real, easy smile spreading across his own face for the first time in months. “I’d like that.”

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