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The Tailor's Intentional Touches

I went for a suit fitting and my tailor started stroking my cock.

5 min read November 01, 2026New

Winston stood on the low wooden podium in nothing but his briefs, the shop’s late light pooling across the pale gray wool of the unfinished jacket draped over a chair. Twenty-eight, broad through the shoulders from years of lifting at the warehouse, he kept his eyes on the far wall and tried not to shift his weight. The room smelled of chalk, steam, and cedar. Bruno moved around him with the tape already in one hand, forty-two and precise, sleeves rolled to the elbow, the gray at his temples catching the lamp. He had been the only tailor Winston trusted with a custom suit, and the fitting had started the way every fitting did: shoulders, chest, waist, the quiet click of pins.

“Arms down,” Bruno said. His voice was low, professional. He slid the tape around Winston’s hips, then lower, checking the seat of the trousers that were not yet cut. His knuckles brushed the inside of Winston’s thigh as he adjusted the fall of the measuring string. Just a graze. Winston felt it anyway, a hot line under the skin. Bruno’s other hand settled at the curve of his ass, palm flat for a second while he pinned a mark in the air with his thumb, then lifted away. Routine. The kind of touch a man learned to ignore in a shop like this.

Winston’s cock did not ignore it. Heat gathered low in his belly. The thin cotton of the briefs clung, and he felt himself thicken against the fabric, a slow, unmistakable swell. He swallowed and stared harder at the wall. Bruno circled again, tape snapping softly. Another pass along the inner thigh, fingers lingering half a second longer than the measurement required, the pad of his thumb skating the seam where leg met groin. Winston’s breath caught. The outline of his shaft pressed forward, stretching the cotton, the head already darkening the cloth. Bruno’s eyes flicked down once, then back to the tape, and the corner of his mouth did not quite move.

“Inseam next,” Bruno murmured. He dropped to one knee without ceremony, the way he always did, and Winston’s pulse jumped so hard he heard it in his ears.

Bruno’s hand settled high on Winston’s inner thigh again, this time with the tape held loose between his fingers so the contact was all skin and warmth through the briefs. He drew the measure down the leg, slow, and on the way back up his knuckles traced the growing ridge of Winston’s cock from root to tip. Not a bump. A stroke. Deliberate enough that Winston’s hips twitched before he could stop them. The cotton dragged over the sensitive underside, and a bead of wetness darkened the fabric at the head.

“You’re filling out,” Bruno said, still quiet, still looking at the tape as if the numbers mattered. His thumb pressed along the shaft through the briefs, a firm, intentional glide that made Winston’s breath leave him in a rush. “Hold still.”

Winston held still. He did not step back. He did not tell the older man to stop. His cock jumped under the next pass, fully hard now, the outline obscene against the thin cotton, the waistband pulled tight. Bruno’s fingers wrapped the length through the fabric and squeezed once, testing, then stroked again from base to crown, slower, the heel of his palm catching the wet spot and smearing it. Winston’s chest rose and fell. He looked down. Bruno looked up. The heat in that glance was plain, no question left in it, and Winston’s nod was small and sure.

“Don’t stop,” Winston said, voice rough.

Bruno’s mouth curved. He stayed on his knees on the worn rug, both hands coming up now, one cupping the heavy weight of Winston’s balls through the briefs, the other working the shaft in long, firm strokes that made the cotton whisper. He squeezed the head, thumb circling the soaked patch, then stroked down hard enough that Winston moaned and pushed his hips forward into the grip. The podium creaked. Bruno’s eyes stayed on his face while he did it again, openly, no pretense of measuring left, milking the thick cock through the clinging fabric until Winston’s thighs trembled and precome soaked through in a dark, spreading stain.

“Look at you,” Bruno said. He hooked his fingers in the waistband. “These are in the way.”

Winston lifted his hips. Bruno tugged the briefs down, past the cock, past the balls, until they caught under the swell of Winston’s ass and the shaft sprang free, thick and flushed, the head glossy and already leaking. Cool air hit the wet skin. Bruno wrapped his fist around the bare shaft and stroked, skin on skin now, slow and tight, watching a fresh bead well at the slit and slide down over his knuckles. He leaned in and licked it off, tongue flat and hot, then opened his mouth and took the head inside.

Winston’s hand found Bruno’s shoulder. The tailor sucked him deep on the first descent, lips stretching around the girth, tongue pressed hard along the underside while his fist kept working what his mouth could not yet take. Wet sounds filled the quiet shop. Bruno pulled back to the crown, swirled his tongue, then sank again, throat working, one hand stroking the shaft in time with each bob of his head. Spit slicked Winston’s cock and ran over Bruno’s fingers. Winston moaned, low and broken, and rocked his hips forward, feeding more of himself into that heat. Bruno took it, eyes half-lidded, cheeks hollowed, the deliberate stroke of his hand never stopping even as he swallowed Winston deeper, nose brushing the trimmed hair at the base, then drawing back to suck hard at the head while his fist pumped the soaked length.

“Fuck,” Winston gasped. His hips jerked. Bruno groaned around him, the vibration running straight up the shaft, and sucked harder, filthy and eager, spit shining on his chin. He stroked faster, twisting his wrist on the upstroke, mouth sealed tight, tongue flicking the slit every time he pulled off to breathe before taking him deep again. Winston’s balls drew up. The pressure coiled, sharp and inevitable. He warned Bruno with a choked sound and a tighter grip on his shoulder, and Bruno only sank lower, hand flying on the shaft, throat open, inviting it.

Winston came hard, cock pulsing, thick spurts flooding Bruno’s mouth and sliding straight down his throat. Bruno swallowed around him, milking every drop with his fist and his tongue, not spilling a thing, sucking through the aftershocks until Winston shuddered and the last weak pulse coated his tongue. He pulled off slow, lips shiny, and licked the head clean with one last filthy swipe.

Bruno stood, wiped his mouth with the back of his hand, and picked up the tape as if the numbers had been waiting. Winston’s cock still hung heavy and wet against his thigh, briefs bunched under his ass, and Bruno’s calm fingers brushed the inside of that thigh again while he marked the inseam, both of them breathing hard and saying nothing. Winston tasted the shop air and the ghost of his own spend on Bruno’s breath when the tailor leaned close to pin the hip.

Bruno licked the last trace of come from his lower lip and said, voice even, “Hold still. I’m not finished measuring that cock.”

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