Cover of The Tailor's Apprentice

The Tailor's Apprentice

Read the story

9 chapters · 38931 words · Read 0 times

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 9: Confrontation

The chill leeched through John’s jacket as they stepped onto the pavement outside the barber’s, the crisp air a shock after the hot towels and steamy atmosphere. He held his arm out, an old-fashioned gesture that felt oddly natural now. Silas hesitated for only a second, his gloved hand coming to rest lightly in the crook of John’s elbow.

“I’m starving,” John said, his breath fogging. “My treat. Let’s get some proper food before we get buried in fabric.”

Silas adjusted his glasses with his free hand. “Your treat necessitates your choice of venue. Show me where John goes. Where his preferences lead.”

“It won’t be some posh gaff,” John warned, steering them down a side street away from the main thoroughfares. “None of that tiny food on big plates.”

A low, rich chuckle escaped Silas. “My dear boy, I have slummed it plenty in my life. Lead on.”

The pie and mash shop was a beacon of warmth, its windows completely fogged over. The bell above the door jangled, and the smell hit them—rich gravy, cooked meat, the sharp tang of malt vinegar, the comforting earthiness of mashed potato. It was crowded, noisy, full of life. They found a small, Formica-topped table near the back, their knees bumping underneath.

John watched with delight as Silas, with fastidious elegance, tackled a steaming mince pie, a mound of mash, and a lake of liquor. He ate with precise, appreciative bites, his dark eyes taking in the bustling room.

“See?” John said, swirling a chip in gravy. “Proper fuel.”

“Indeed,” Silas agreed, dabbing his thin lips with a paper napkin. “Superior to any fussy amuse-bouche.”

The hearty food and the easy intimacy loosened John’s tongue. He leaned forward, his voice dropping. “Can I ask you something? And don’t tell me to stop mockin’ you.”

Silas raised a silver eyebrow.

“Back at the gym,” John continued, his blue eyes intent. “In the locker room. And even now, just walkin’. You really don’t see it, do you? How men look at you.”

Silas put his fork down. “John.”

“No, listen. I know that look. It’s the same look I get when I want to fuck someone into next week.” He held Silas’s gaze, not letting him look away. “It’s the look I’m givin’ you right now.”

A faint, crimson flush crept up Silas’s neck, visible above his crisp collar. He said nothing, but his stillness was an admission.

John smiled, easy and warm. “Next time we’re at the gym, I’ll point ‘em out. The lads watching you. The ones imagining you on your knees.” He leaned closer still, his voice a rough whisper barely audible over the clatter of plates. “Don’t tell me you wouldn’t like it. A few thick cocks filling you up while you’ve got your lips stretched around mine. Getting used like a proper fuck-toy.”

Silas made a small, choked sound, half-gasp, half-giggle. He looked down at his empty plate, the blush now full across his aristocratic cheeks. He didn’t reply.

After a moment, he cleared his throat, the picture of regained composure. “We have tasks this afternoon. I must finish the waistcoat for tomorrow’s client. And you have your practice. Your education continues.”

They paid and stepped back into the grey afternoon, walking slowly towards the shop. “This client,” John asked, his arm offered again and taken. “Why the big discretion? You said I’d recognise him.”

“You will. And his… tastes are specific. He enjoys a profound stretch. He likes to give, and he very much likes to receive.” Silas shot him a sidelong glance. “He will enjoy kneeling beside me, I think, while you work your hands into both of us. Your technique is coming along. It’s raw, but powerful.”

John felt his cock thicken instantly, pressing against his jeans. The image was immediate and visceral: Silas on all fours, another man—someone he knew from the telly, maybe, or the news—kneeling right there, both of them open and wanting, taking his fist. The sheer, deviant power of it made his mouth go dry.

But another thought, quieter, followed. He remembered the searing, full feeling of Silas’s mouth on him in their bedroom, the clever tongue probing his entrance, the shocking mindless pleasure of Silas's mouth working his hole for what felt like hours. He remembered the euphoric abandon on Silas’s face when he took John’s entire fist, the way his body had convulsed with a pleasure so deep it seemed spiritual.

“What about…” John began, his voice uncharacteristically tentative. “What about receiving? For me, I mean.”

Silas stopped walking. They were a block from the shop. He turned to look at John, his black eyes searching. “It’s not a small thing, John.”

“I know. I’ve seen what it does to you. I felt… I liked what you did to me. Just the start of it.” He shrugged, a bit of his usual bravado returning. “Might be worth a proper go.”

“It requires time,” Silas said slowly, precisely. “Patience. Trust. It is a landscape of sensation, not a conquest.” He started walking again, his pace measured. “We could explore it. In private. Slowly. And you say ‘stop’, and everything stops. That is the only rule.”

“Could we… try a bit? Tonight?” John asked, the eagerness clear in his voice.

Silas’s hand tightened on his arm. John saw the older man’s free hand subtly adjust the front of his tailored trousers. “I would be delighted,” Silas said, his baritone a little thick. “Provided, of course, you open me up thoroughly afterwards. A fair trade.”

“Fuck yeah,” John grinned. “It’s a deal.”

They turned the final corner, the familiar frontage of Blackwood Tailoring coming into view. The momentum of their arrangement, the warm, full feeling from the food and the illicit plans, propelled John forward.

Then he stopped.

Silas stopped a half-step later, his grip on John’s arm turning rigid.

A woman was leaning against the shop’s dark green door, arms folded against the cold. She was hugging a cheap polyester coat around herself, her posture radiating frustration and a deep, weary anger. Her eyes, the same bright blue as John’s but now hardened, locked onto him. Then they flicked to Silas, to their linked arms, and back to John. Her expression didn’t change, but something behind her eyes shut down completely.

“John,” Karen said. Her voice was flat, a worn-out blade.

All the warmth bled from John’s world. The imagined heat of Silas’s apartment, the phantom tastes of gravy and illicit desire, vanished, replaced by the stark, cold reality of his wife’s face. He held on to Silas’s arm as if it were his life support.

“Karen.” The name felt alien in his mouth. “What are you doing here?”

“Looking for my husband,” she said, pushing off the door. “Your phone’s off. Again. The landlord came by. Again.” She finally acknowledged Silas with a curt, devastatingly polite nod. “Mr. Blackwood. I've heard about you. The tailoring apprenticeship.” She infused the word with a universe of sarcastic implication.

Silas offered a shallow, equally polite bow of his head. “Mrs. Henderson. A pleasure, albeit unexpected.” His voice was smooth as polished glass, giving nothing away. “If you’ll excuse me, I have work to attend to.” He produced his keys, moving past her to unlock the shop door. He paused, his hand on the knob, and looked at John. The message in his eyes was clear: This is yours to manage. “Do take the time you need, John. Our tasks can wait.”

The door closed behind Silas with a definitive click, leaving John alone on the pavement with the ghost of his old life.

“You look different,” Karen said, her eyes scanning him. The new, sharper haircut, the better jacket, the subtle aura of confidence that came from being consistently desired. “You look pleased with yourself.”

“It’s a job, Karen,” he said, the defensiveness rising in his throat like bile. “A proper one. I’m learning.”

“Learning what?” she shot back, a brittle laugh escaping her. “How to measure inside legs? Is that why you left because I just don't have the equipment you need?” She took a step closer, her voice dropping to a fierce whisper. “I’m not stupid, John. I called the gym. You haven’t been for over a month. No one has seen you. So where are you staying?”

The lie he’d been nursing curdled inside him. He thought of the locker room, the smell of leather and musk, the brutal, passionate rhythm of Silas moving inside him. He thought of the client coming tomorrow who liked to be fisted. He thought of his own secret curiosity, the pact he’d just made for the night.

He looked at Karen’s face, the lines of disappointment etched around her mouth, the fading hope in her eyes. She was the linchpin of the world he was supposed to want. The world that felt, more each day, like a poorly tailored suit he’d outgrown.

“It’s complicated,” he said, the words utterly inadequate.

“Un-complicate it,” she demanded, tears of fury now glittering in her eyes. “Come home. Now. Don't abandon us for some moment of insanity.”

"No," John said firmly. "This is my life now. I've never been happier. I know that must hurt, but it's the truth, Karen."

"No wonder you were so shit in bed then, if you're a fucking bender."

She turned and walked away, her footsteps echoing on the wet pavement. John didn’t follow. He watched her go, a cold knot tightening in his stomach where the pie and mash and the heat of promise had just been. The shop door behind him seemed to pulse, a dark mouth leading to a world of terrifying, exquisite freedom. Karen’s figure shrunk, blurred, and turned the corner.

He was still standing there, staring at nothing, when the shop door opened silently behind him.

Silas didn’t speak. He simply stood in the threshold, a silhouette against the warm, dim light of the shop. An invitation. A question.

John took a deep, shuddering breath of the cold London air, tasted the ending of one life and the terrifying birth of another. Without looking back, he stepped across the threshold. The door closed, sealing him in the quiet, cloth-dusted silence.

Inside, Silas was already removing his coat, his movements economical. “The choice presents itself,” he said, not looking at John as he hung the coat neatly. “The known misery, or the unknown ecstasy.” He finally turned, his black eyes capturing John’s. “There is no shame in choosing the former. It is the wider path.”

John’s heart hammered against his ribs. He could still smell the pie shop on his clothes. He could still see Karen’s wounded face. But stronger was the memory of Silas’s breath hot on his neck, the promise of a slow, patient exploration of his own body, the shocking sensation of being utterly filled.

“I’m not going back,” John said, the words surprising him with their finality. "That isn't my life. That isn't who I am. I belong here. With you."

With you."

The words hung in the quiet shop, solid and final. For a long moment, Silas didn’t move. Then a tremor passed through his precise frame. He removed his wire glasses, polished them slowly on his waistcoat, and John saw the sheen in his obsidian eyes, the liquid gathering along his lower lids. Silas was a man of contained histories and measured gestures, and this unchecked moisture was a fissure in his facade, profound and terrifying.

John’s own composure cracked at the sight. A rough sound escaped his throat, part sob, part gasp. He crossed the space between them in two strides, the bolts of superfine wool and shelves of thread blurring into irrelevance. He didn’t hug; he enveloped, his strong, hairy arms closing around Silas’s slender back, pulling him in until John could feel the frantic beat of the older man’s heart against his own chest. Silas shuddered, his face pressed into John’s neck, his carefully combed silver hair disarranged by the force of John’s chin.

“I wouldn’t blame you,” Silas whispered into his skin, the words hot and damp. “If you walked out that door. If you chose the easier, simpler fiction. It is the rational choice, John.”

John held him tighter, his own eyes squeezing shut against a surge of protectiveness so fierce it winded him. “Shut up,” he murmured, his voice thick. “Just shut up. I’d never forgive myself. You hear me? Never.” He leaned back, cupping Silas’s stubbled jaw in his broad hand, forcing him to meet his gaze. “This thing between us… it’s the first real thing I’ve ever had that’s mine. That I actually want to fight for. You are mine, Silas. And I am never letting go of that. Ever.”

Silas stared, his piercing eyes searching John’s face, scanning for doubt, for the inevitable flinch, for the societal programming that should have been clicking into place. He found only a stubborn, blazing certainty. A tear broke free, tracing a clean path down his cheek. “How are you real, Jonathan?” he breathed, the formal name a testament to the moment’s gravity. “How are you not made of smoke and mirrors? A phantom of wishful thinking?”

John wiped the tear away with his thumb, his calloused skin rasping against Silas’s fine pores. “I needed someone to find me,” John said, the simplicity of it stunning him as he spoke. “In all that fucking noise of my life. And you… you found me.”

Their lips met softly, a dry, closed-mouth press that spoke of sealing a pact, not stoking a fire. It was tender, lingering, a silent conversation of palms flat against backs and steadying breaths. When they parted, Silas rested his forehead against John’s, his composure returning in a slow, deliberate inhale.

“We should work,” Silas suggested, his voice regaining its rich, quiet timbre. “Not to forget. To let our hands parse what our minds need to understand.” He made tea, the ritual of boiling kettle and steeping leaves a grounding anchor in the emotional upheaval. They sat at the large cutting table, the waistcoat between them, and for three hours, the only sounds were the snipping of scissors, the pull of thread through cloth, and the occasional sip from a china cup.

Silas finally stretched, rolling his shoulders back with a soft sigh of satisfaction. The waistcoat was finished, a masterpiece of midnight blue jacquard, ready for tomorrow’s discreet client. He picked up John’s practice piece, a strip of charcoal grey wool studded with a line of hand-stitched buttonholes.

“These are excellent, John,” he said, genuine admiration in his tone. He traced one with a fingertip. “This one’s tension is slightly inconsistent here, see? But your instinct is there. You have a feel for it. You’re very good at this.”

A slow, wicked grin spread across John’s face, the emotional intensity of the afternoon transmuting into a pure, carnal spike. “Good enough to get my hole stretched out by the hottest man in town?”

Silas’s eyes darkened. He leaned in, his lips brushing the shell of John’s ear, his whisper a hot, promising vibration. “Absolutely.”

He captured John’s mouth, this time with a hungry, searching passion, their tongues tangling deeply. Silas stood, pulling John up with him, and led him by the hand through the curtain and up the narrow stairs to his cluttered apartment.

“Bathroom,” Silas directed, his voice already assuming a gentle command. “Clean yourself thoroughly. I will prepare.”

In the bedroom, Silas opened a small, polished wooden case lined with purple velvet. He selected several silicone toys, graduated in size, and a bottle of clear, viscous lubricant. He arranged them on the nightstand alongside a fresh towel. He stripped slowly, folding his clothes over a chair, his body pale and lean in the dim light.

John returned, damp and naked, his muscular, hairy body a stark contrast to Silas’s refined lines. He was already half-hard, his thick cock curving up against his belly.

“On the bed,” Silas said. “On your knees. Head down, arse up. Present yourself.”

John obeyed, the submission thrilling him. He heard the click of the lubricant cap, then felt Silas’s cool, skilled hands spreading his cheeks wide. Silas exhaled, a sound of pure reverence.

“Beautiful,” he murmured, before his tongue, flat and warm, swiped up from John’s taint to the very top of his cleft.

John groaned, his fists clutching the duvet. Silas ate him with a devoted, unhurried intensity, his tongue circling the tight furl of muscle, dipping shallowly inside, painting him with wet, hot attention. He alternated broad, languid strokes with pointed, probing flicks, until John was shuddering, his cock fully erect and dripping pre-come onto the sheets below.

“So responsive,” Silas whispered, his breath ghosting over the wetness. “This gorgeous, greedy hole. It’s begging for it, isn’t it?”

“Yeah, fuck, yes it is,” John panted, pushing back slightly.

The first touch of cold lube made him jump. Silas warmed it between his fingers, then began to massage the tight ring, his finger pads slick and insistent. He worked in slow, relentless circles, applying steady pressure until, with a soft, yielding pop, the tip of his index finger slipped inside.

“Breathe out, John,” Silas soothed, curling his finger, finding the sweet, electric spot within. “That’s it. Take it. Just my finger, fucking you open. Imagine it’s my tongue, deeper than I can reach.”

He added a second finger, scissoring them gently, the stretch a bright, undeniable fullness. John buried his face in the bedding, grunting with each deliberate movement.

“Now for something more substantial,” Silas purred, retrieving the smallest toy, a sleek, tapered shape. He coated it generously, the lube dripping down John’s perineum. “This is just a greeting. A hello from the wider world.” He pressed the blunt tip against John’s entrance, which now pulsed around nothing. “Push out against it, John. Like you’re taking a shit. Good. Just like that.”

The toy slid in with surprising ease, the thickest part passing his rim with a stretch that made John shout. It was solid, unyielding.

“Feel that?” Silas whispered, beginning a slow, pistoning rhythm. “That’s the beginning. That’s just a taste of what your body can learn to crave. You’re swallowing it so well. Such a good, hungry slut for this, aren’t you?”

“Fuck, Silas… yes.”

Silas worked him relentlessly, alternating the toy’s thrusts with the swirl of his fingers, constantly whispering filth. “You want the next one, don’t you? You want it deeper. You want me to make this hole a proper sheath. You want to be my open, used boy.”

John could only nod, his mind hazy with sensation, his cock an angry, leaking rod of need. The second toy was a significant leap, a thick, bulbous-headed invader. The initial resistance was intense, a burning pressure that stole his breath.

“Breathe,” Silas commanded, his voice calm and absolute. He didn’t force it. He just held the pressure, letting John’s body acclimatize, gradually accepting the impossible girth until, with a gasp, the head popped in and the rest followed smoothly. “Oh, look at you. Taking it like a champion. Your hole is swallowing this whole. Look at how it grips.”

By the time Silas coated the third toy, John was sweating, trembling, a puppet of pure sensation. This one was longer, with a pronounced curve. Silas fed it to him slowly, relentlessly, until it was seated fully, massaging his prostate with every subtle movement. John was babbling, a stream of “fuck” and “oh god” and “more”.

Silas stilled, leaving the toy buried to the hilt. He leaned over, kissing the sweat-damped small of John’s back. “Enough. That’s your limit for today. And you did magnificently.”

He carefully withdrew the toy, and John collapsed onto his side, spent and buzzing. Silas lay beside him, and they kissed like teenagers, all soft lips and shared breath, a gentle counterpoint to the intense violation. After a few minutes, John’s energy returned, that relentless urge to give, to dominate, to reciprocate.

“My turn,” John growled, rolling Silas onto his back. “I need to feel you. All of you.”

They switched places. John took his time, worshipping Silas’s body with his mouth and hands, before concentrating on his goal. He started with three fingers, then four, Silas’s body a familiar, welcoming landscape. He used more lube, working it in with a gentle, corkscrewing motion. He moved to a small, knobbly toy, then a medium one, all the while watching Silas’s face, listening to his hitched breaths and whimpered pleas.

“Now,” Silas finally gasped, his legs splayed wide. “Your hand. Please, John.”

John lubed his entire right hand, wrist, and forearm. He pressed his fingers together into a tight beak, the heel of his palm leading. He pressed against Silas’s loosened, glistening entrance.

The acceptance was slow, milimetre by milimetre. John leaned his weight into it, watching the incredible sight of Silas’s body opening for him, the muscle distending to accommodate the widest part of his hand. Silas cried out, a sharp, ecstatic sound, as John’s hand sank in up to the wrist.

“Jesus Christ,” John breathed, awestruck by the heat, the tight, muscular clench around his fist. He began to move, a gentle fucking motion, his knuckles brushing Silas’s inner walls. Silas was chanting, a stream of “yes” and “more” and “deeper”.

Feeling the incredible yielding, John did not stop at the wrist. He angled his arm slightly, and with one last, steady push, another inch of his corded forearm slid inside. Silas’s body arched off the bed, a silent scream on his lips, his eyes rolled back in overwhelming sensation. John held there, feeling the frantic pulse around his embedded limb, knowing he had found the limit.

After a moment of perfect, stretched stillness, John slowly withdrew his arm. Silas’s hole gaped, swollen and shining, a flushed, open o. John was on him in an instant, his own cock, thick and desperate, nudging at that impossible looseness.

“Gonna fill you up,” John grunted, and pushed inside in one smooth, staggering plunge. There was no resistance, only wet, silken heat, overwhelmingly deep. He fucked him with hard, driving strokes, the slap of flesh and Silas’s ragged cries filling the room. The coiling tension in John’s gut tightened unbearably.

“Gonna come,” he warned, pulling out abruptly. His cock, slick with lube and Silas, erupted in thick, white ropes that splattered across Silas’s stretched, quivering hole and his trembling cheeks.

Without hesitation, John dove down, his mouth sealing over the mess. He licked fervently, cleaning his own spend from Silas’s sensitive skin, his tongue probing the exposed, tender opening. At the same time, his lubed hand closed around Silas’s leaking cock, jerking it in firm, fast strokes.

The dual assault—the filthy, intimate kiss at his ravaged entrance and the ruthless friction on his cock—sent Silas over the edge. He came with a broken shout, his release painting his stomach in violent pulses, his whole body seizing as John drank from him, worshipped him, owned him completely in the quiet, messy aftermath.

Read on DreamPress

Write your own erotic story with AI