My Tailor Fills My Bound Ass

Felix, the 28-year-old corporate executive whose days were spent barking orders across glass conference tables and crushing competitors in boardroom battles, felt his pulse hammer in his throat as he rapped his knuckles on the glass door of the tailor shop. The city street was quiet, the “Closed” sign already flipped. This was their arrangement for the final fitting—after hours, just the two of them in the back room where the air always smelled of fresh wool, steam, and something darker, something male.

Theo opened the door. The 35-year-old master tailor wore a crisp white shirt with the sleeves rolled high on his thick forearms, the fabric stretched across a chest that spoke of years spent lifting heavy bolts of cloth and even heavier clients’ expectations. His dark eyes swept over Felix once, slow and assessing, before he stepped aside. “Come through. Pants are ready on the form. Let’s get you pinned.”

The back room swallowed them. Mirrors lined three walls. A wide oak table held scissors, chalk, and coils of spare twine that suddenly looked far more interesting to Felix than they ever had before. He stripped off his bespoke jacket, then his shirt, leaving only the half-finished charcoal trousers Theo had basted together. The wool was still loose in places, raw edges waiting for final seams. Felix stepped into them, the cool lining sliding up his legs and cupping his ass like a promise. He climbed onto the low fitting platform and stood still, hands at his sides, already half-hard beneath the fabric.

Theo moved behind him. The first pins went into the waistband with crisp little clicks. Professional. Precise. Then the tailor’s hands dropped lower, smoothing the seat of the trousers. Those strong fingers lingered. They pressed. They traced the cleft of Felix’s ass through the wool, thumbs spreading just enough to make the fabric pull tight over his hole.

Felix’s breath stuttered. “You’re not measuring anymore, are you?”

“No.” Theo’s voice was low, roughened by years of smoking expensive cigarettes and giving orders of his own. “I’m deciding how much longer I can pretend I don’t want to wreck this perfect executive ass.” His palms cupped both cheeks fully now, squeezing, kneading the firm muscle until Felix’s cock jerked visibly against the front of the half-finished pants. “Every time you’ve stood here these past months, I’ve imagined bending you over this platform, ripping these trousers down, and burying my cock so deep you forget your own name.”

Felix’s mouth went dry. The words he had rehearsed in his head for weeks spilled out in a rush. “Then stop imagining. I don’t want the suit. I want you. Rough. Raw. I want you to dominate me completely. Tie me up so I can’t move and fuck my ass like it belongs to you. No mercy. No condom. Just your thick cock stretching me open and filling me until I’m dripping.” His voice cracked with need. “Please, Theo. I’ve been aching for it. I need to be used.”

Theo’s grip tightened hard enough to leave marks through the wool. A low, filthy chuckle vibrated against Felix’s ear. “Careful what you beg for, boy. Once I start, that tight little hole is going to be ruined for anyone else. I’m going to tie your wrists so tight the rope bites, shove your face down on that table, and pound you raw until your legs shake and you’re sobbing for my load. You want that? You want your tailor to turn you into his personal cum-dump?”

“Yes,” Felix hissed, hips pushing back into those squeezing hands. “God, yes. I run an empire all day. Tonight I want to be your bound fucktoy. Wreck me. Own me.”

Theo spun him around so fast Felix nearly lost balance. The older man’s eyes were black with lust, pupils blown wide. He palmed Felix’s ass again, this time from the front, fingers digging into the meat of his cheeks and spreading them obscenely through the trousers. The half-pinned seams strained. “Feel that? That’s my property now. I’m going to rip these pants down, spit on your hole, and shove every inch of my cock inside you bare. You’ll take it all—every thick vein, every brutal thrust. I’m going to fuck you so deep my balls slap your taint while you’re tied and helpless. You’ll feel me for days. Every time you sit in one of your fancy meetings, you’ll be leaking my cum and remembering exactly who owns this greedy executive ass.”

Felix’s knees buckled. He dropped right there on the platform, the rough carpet biting into his shins. His hands shook as he tore at Theo’s belt, yanked the zipper down, and freed the tailor’s cock. It was thicker than he had imagined—veined, heavy, the head already slick and flushed dark red. The scent of Theo—clean sweat, cologne, and pure aroused male—hit him like a drug.

He didn’t tease. He swallowed Theo’s cock in one sloppy, greedy plunge, lips stretching wide, throat convulsing. Saliva immediately spilled from the corners of his mouth, dripping onto the half-finished trousers as he bobbed frantically. Wet, obscene sounds filled the back room: gagging, slurping, the slick pop every time he pulled off to gasp for air.

“Fuck—yes, just like that,” Theo growled, one hand fisting in Felix’s perfectly styled hair, ruining it. “Look at you. Corporate hotshot on his knees sucking tailor cock like a desperate whore. Louder. I want to hear how much you need it.”

Felix pulled off just long enough to beg, strings of spit connecting his swollen lips to the glistening shaft. “Tie me up. Please. Get the twine, the measuring tape, whatever—bind my wrists behind my back and use me. I want to be helpless while you wreck my hole. I want you to slap my face with this fat cock and tell me what a filthy bottom I am. I want you to raw-fuck me until I can’t walk.” He dove back down, taking Theo to the root, nose pressed to the crisp dark hair at the base, throat working around the thick intrusion.

Theo’s hips snapped forward, fucking Felix’s face with controlled power. “You’re going to get exactly what you’re begging for. I’m going to truss you like a present, bend you over that table, and split your ass open. No warm-up. Just my cock and your greedy, clenching hole. You’ll take every inch raw, and you’ll thank me for it. Because that’s what you are tonight, Felix—my tied-up, ass-up cumslut.”

Felix moaned around the cock stuffing his mouth, the vibration making Theo curse. His own dick strained painfully against the wool trousers, leaking steadily, soaking through. Every filthy promise sent another bolt of heat through his gut. He had spent years dominating conference rooms; the relief of handing that power over to this older, stronger man was dizzying. He sucked harder, hollowing his cheeks, tongue swirling the fat vein underneath, desperate to prove how badly he wanted to be broken.

Theo’s grip in his hair tightened to the edge of pain. He held Felix down on his cock until the younger man’s eyes watered, then pulled him off with a wet gasp. Strings of saliva hung from Felix’s chin, dripping onto his bare chest. The tailor’s voice was dark velvet and steel. “Up. We’re not done with your mouth yet, but I want those hands tied before I bend you over. You’re going to keep begging while I bind you. I want to hear exactly how you want this ass destroyed.”

Felix rose on shaky legs, lips shiny and bruised, eyes glazed with lust. His trousers were tented obscenely, the half-finished seams straining. Theo reached for the coil of strong twine on the worktable, eyes never leaving Felix’s face. The air between them crackled, thick with the promise of rope, sweat, and raw, relentless fucking still to come.

The tension stretched taut as Theo slowly unwound the twine, letting it whisper against itself. Felix’s chest heaved, heart slamming against his ribs, every nerve screaming for the moment those rough hands would finally bind him helpless and deliver on every filthy word.

Theo set the twine aside without a word, his thick fingers instead closing around the long leather measuring tape that dangled from its hook on the worktable. The material was supple from decades of use, yet sturdy enough to bite when pulled tight. Felix’s breath hitched as the 35-year-old tailor circled behind him, the older man’s chest brushing his bound shoulders. Theo drew Felix’s arms back with firm care, giving him one heartbeat to adjust before wrapping the leather tape around both wrists three times. He cinched it hard, the edges digging into skin with a sharp, perfect pressure that made Felix’s cock jerk against the half-finished trousers. The restraint locked his shoulders back, chest thrust out, every small tug sending sparks of heat straight to his groin.

This is everything I’ve craved, Felix thought, the 28-year-old executive who spent his days commanding rooms now utterly helpless in the back of a tailor shop that smelled of wool, steam, and raw male sweat. The leather bit deeper as Theo knotted it with deliberate care, testing the hold by sliding two fingers beneath the wraps. “Too much?” Theo asked, voice gravel-rough.

“Tighter,” Felix begged, hips already rolling back in invitation. “I want to feel it every time you thrust. Make me yours.”

Theo obliged, yanking the final knot until the tape creaked. “There. Wrists locked behind your back like the eager fucktoy you are. No moving. No escaping. This executive ass is my property now.” He ran a possessive palm down Felix’s spine, then gripped his shoulders and bent him forward over the low fitting platform. The padded top met Felix’s chest with cool firmness; his cheek pressed to the fabric, ass shoved high. The surrounding mirrors showed every angle—the 28-year-old’s flushed face, his bound wrists crossed tight, the half-basted charcoal wool straining over his spread thighs. Theo loomed behind him, sleeves rolled high on powerful forearms, cock still wet from Felix’s throat and standing thick and flushed.

With a low growl, Theo seized the waistband of the trousers and ripped downward in one savage motion. Basted seams tore with a loud, obscene rip, pins scattering across the floor like tiny metallic rain. The wool shredded down Felix’s legs and pooled at his ankles, leaving him naked from the waist down, cock leaking steadily onto the platform, hole exposed and clenching under the tailor’s gaze.

Theo spread his cheeks wide, thumbs digging into firm muscle. “Look at this perfect hole. Been dreaming about it for months.” He hawked loudly and spat directly onto the tight pucker, the warm glob landing with a wet smack and sliding down over sensitive skin. Felix moaned at the filthy sensation. Two of Theo’s thick fingers followed immediately, pressing past the spit-slick ring without pause. The stretch burned raw and real, the digits sinking deep, scissoring apart, curling hard against his prostate. Wet sounds filled the room as Theo finger-fucked him with steady, brutal strokes, stretching the muscle until it fluttered greedily around the intrusion.

“Fuck—Theo—your fingers are so thick,” Felix gasped, voice breaking. The burn melted into liquid pleasure that made his bound arms strain against the leather tape. Every curl of those fingers sent electricity up his spine. I run billion-dollar deals and now I’m bent over a tailor’s platform with my ass full of his spit and fingers. This is what I needed. To be used. “Deeper. Open me. I want to feel you for a week.”

“You’ll feel me for a month,” Theo snarled, pumping harder, twisting his wrist so the knuckles stretched him wider. “This greedy hole is already sucking me in. Corporate boy comes in here acting professional, but all you want is to be tied and raw-fucked like a common slut. Say it.”

“I’m your tied-up slut,” Felix panted, pushing back onto the fingers, mirrors reflecting the way his hole glistened and clung. “Wreck me raw. Please.”

Theo pulled his fingers free with a wet pop, leaving Felix empty and aching. The blunt, fat head of his bare cock replaced them at once. Theo gripped Felix’s hips hard enough to bruise, lined up, and slammed forward in one merciless thrust. Balls-deep in a single stroke, the thick cock speared him open, raw skin dragging along sensitive walls, veins pulsing against his rim. Felix cried out at the sudden fullness, the burn sharper without a condom, exactly as he had begged.

Theo gave him no mercy. He started a brutal standing doggy-style fuck, hips snapping forward with powerful, punishing strokes. The wet slap of his heavy balls against Felix’s taint echoed off the mirrors. Each thrust drove the air from Felix’s lungs, the platform creaking beneath them. Sweat broke out across Felix’s back as Theo railed him, the older man’s shirt sticking to his muscular chest.

“Take every inch, you bound whore,” Theo growled, never slowing. “Feel that? My raw cock owning your tailor-made fuckhole. I measured this ass for months and now I’m finally stretching it the way it deserves. Greedy fucking hole—look how it swallows me. You’re going to leak my cum for days while you sit in your fancy meetings pretending you’re still in charge.”

Felix’s thoughts fractured under the onslaught. The leather tape dug into his wrists with every jolt, a constant reminder of his helplessness. The raw drag of Theo’s thick cock lit up every nerve; the head battered his prostate on every deep plunge, sending pulses of pleasure so intense his own untouched dick swung and dripped beneath him. In the mirrors he watched himself get fucked—face slack, mouth open, body jolting forward with each brutal impact. The scent of wool and male arousal thickened the air. “Harder,” he moaned. “Ruin me. I’m your cumslut tonight.”

Theo laughed darkly and obliged, shifting his angle until every thrust nailed Felix’s prostate dead-on. The pace grew faster, filthier, the sound of sweat-slick skin slapping loud and rhythmic. “That’s right. Feel me rearrange your guts. This hole was made for my cock. I’m going to flood it so full you’ll feel me every time you move.”

After long minutes of relentless pounding that left Felix’s legs trembling, Theo suddenly pulled out. The loss drew a desperate whine from Felix’s throat. The tailor flipped him onto his back on the wide platform as if he weighed nothing, shoving his bound arms overhead and pinning both wrists down with one iron grip. Felix’s legs were pushed back toward his shoulders, folding him in half. Theo’s slick, angry cock found his wrecked hole again and drove back inside in one deep thrust, now in an intense missionary position that let their eyes lock.

The new angle was devastating. Theo’s hips rolled with powerful strokes, cock sinking impossibly deeper, grinding against Felix’s prostate on every withdrawal and slam. The leather tape bit into Felix’s wrists under Theo’s palm as the older man used his free hand to hold one of Felix’s thighs open wide.

“Look at me while I stretch this greedy tailor-made fuckhole,” Theo snarled, voice low and degrading. “I basted these trousers around the very ass I’m ruining. Every pin, every stitch was just foreplay. Now you’re taking me raw and bare like the desperate executive bottom you really are. This hole was measured for my cock and it fits perfectly—gaping, clenching, milking me. You’re going to cum untouched, boy. Shoot your load all over yourself while I pound my property.”

Felix’s world narrowed to the thick cock splitting him open and the degrading words washing over him. Theo’s hips snapped with precision, nailing his prostate relentlessly. The pressure built unbearably fast, his own cock trapped between their sweat-slick bodies, bouncing untouched but leaking constantly. Every thrust forced moans from his throat; the mirrors showed Theo’s powerful body working above him, muscles flexing, dark eyes locked on Felix’s face with raw ownership.

“Greedy little fuckhole,” Theo continued, voice roughening. “Stretching so wide around me. You run the world all day and at night you beg to be tied and used like this. Cum for me. Show me how much you love being my bound tailor’s cum-dump.”

The words and the relentless pounding against his prostate shoved Felix over the edge. His entire body locked up, hole clamping down hard around Theo’s cock as he came untouched. Thick ropes of cum erupted from his cock, splattering across his own chest and abs in pulsing waves, the orgasm ripping through him so hard his vision whited out. He cried out Theo’s name, ass spasming wildly around the invading shaft.

Theo fucked him through every contraction, growling praise and filth until Felix was whimpering and oversensitive. Only then did the tailor pull out with a wet sound, rising to stroke his glistening cock with fast, urgent strokes. With a guttural groan he came, painting Felix’s bound and wrecked ass with thick, heavy ropes of cum. The first powerful jets landed directly across the gaping, twitching hole, coating it white. More stripes painted his spread cheeks, his taint, even splashing up onto his bound wrists and the small of his back. Theo milked every drop, marking him thoroughly.

Breathing hard, Theo set his spent cock aside and carefully unwrapped the leather measuring tape from Felix’s wrists. His touch turned gentle, thumbs rubbing the deep red marks left behind, soothing the skin with slow circles. He helped the younger man sit up, then stand. Felix’s legs were shaking so badly he nearly collapsed; Theo’s strong arm wrapped around his waist, holding him steady while cum dripped down his thighs.

They stood chest to chest for a long moment before Theo cupped Felix’s jaw and pulled him into a rough, satisfied kiss. It was all tongue and teeth and lingering heat, a raw claiming that left them both breathless when they finally broke apart.

“The finished suit will be ready next week,” Theo murmured against his swollen lips, voice still rough with satisfaction. “Come by for pickup… and another private fitting. I’ll have the tape ready.”

Felix left the shop knowing the suit would never be just clothing again.