Gay Boy Milked Like a Cow on All Fours

Rupert’s cock was already leaking before he finished stripping. At twenty-four he had spent the whole day hard and forbidden to touch, and the private playroom in their apartment made the ache worse the second he walked in. Gareth, twenty-nine, had locked the door, killed the overheads, and left only the amber lamps. The padded floor mats were down wall to wall. A clean metal pail waited to one side. On a towel sat the cow-ear headband, the heavy tail plug, the weighted clamps, and the thick leather collar, everything laid out exactly as they had agreed.

“Strip,” Gareth said.

Rupert obeyed. Shirt, pants, socks, nothing underneath. His cock sprang free, thick and flushed dark, a bead of precum shining at the slit and stretching into a thin string when he shifted. He dropped to his hands and knees on the padded floor without being told twice. The mat gave under his palms. He reached for the headband and fitted the cow ears over his own, settling the band until the pale tips brushed his hair. Then he took the plug, already slick, reached back, and worked it into his ass himself while Gareth watched from the edge of the mat. The stretch burned sweet. Rupert breathed, pushed, paused, pushed again, until the widest part popped in and the dark tail hung between his thighs. His cock jerked and drooled another fat drop onto the padding.

Gareth did not help. Arms folded, jaw tight, the front of his own pants strained, he only watched. The air between them was thick with mutual hunger and the bright, shaking tension of Rupert’s untouched cock dripping in open anticipation. Rupert arched, tail swaying, ears tipped forward, and waited to be used.

Gareth circled him slow. Boots quiet on the mat. One hand trailed the line of Rupert’s spine, not quite a caress, more an inspection. He stopped at Rupert’s side, pinched a nipple until it peaked, and closed the first weighted clamp around it. The bite made Rupert gasp and rock forward. The second clamp went on just as mean. The little weights tugged, swinging when Rupert breathed, turning his chest into something that felt heavy and swollen and meant to be pulled.

“There,” Gareth murmured, filthy and fond in the same breath. “Look at those udders. Soft little tits on my eager cow, already trying to give. You’re going to fill that bucket tonight. Every drop. Hands and knees, tail in, ears on, cock hanging down like you were built for the pail.”

He buckled the heavy leather collar snug around Rupert’s throat and gave the ring a testing tug. Rupert’s moan cracked. Gareth walked another slow circle, palm sliding over a flank, thumb pressing the base of the tail so the plug shifted inside him. He flicked a clamp weight and watched Rupert’s cock jump and spit a fresh string of precum toward the mat.

“Dripping already and I haven’t even milked you. Pathetic little dairy slut. All day untouched so you’d be this desperate. You want those udders worked? You want me squeezing that cock like a teat until you squirt in the bucket like livestock?”

“Yes,” Rupert said, voice wrecked. “Please. Milk me. I need it. I’ve been aching. Please milk me like a cow.”

Gareth crouched by his face, grabbed his chin, and made him hold eye contact. “Say it right. Beg like the animal you are.”

Rupert’s arms trembled. The clamps swung. The tail plug sat deep and mean. His cock throbbed, untouched, leaking in long clear strands. “Please milk me like a cow on all fours. Please work my cock and make me give it all in the pail. I’ll moo. I’ll stay down. I’ll be your good cow. Just milk me. Please, Gareth, milk your boy.”

Gareth’s smile was dark and satisfied. “That’s my eager little heifer. Stay exactly like that. Don’t you dare touch yourself. The only hands on that cock are mine.”

He moved behind Rupert and knelt. One broad hand closed around the root of Rupert’s throbbing cock, the other gripped the tail. He did not stroke yet. He held, squeezed once, and felt the pulse kick against his palm while Rupert shook and tried not to thrust.

“Good boy,” Gareth said. “Hold still and get milked.”

Then he started. Long pulls, root to tip, slow and deliberate, the kind of squeeze that emptied rather than teased. His fist dragged the slick skin up, paused under the head, and milked downward again, coaxing another fat bead from the slit and smearing it along the shaft so the next pull was wetter, louder. At the same time his other hand tugged the tail plug, drawing it out until the widest part stretched Rupert’s rim, then pushing it back in with a steady, filthy rhythm. In and out. Stroke and squeeze. The plug kissed his prostate on every deep seat, and the milking hand never let the cock go soft for a second.

Rupert moaned loud, the sound breaking into something helpless. He stayed on all fours. Palms planted. Knees spread. Back arched so his ass stayed offered and his cock hung down where Gareth could work it like a teat. The clamps swung and bit. The collar sat heavy at his throat. Every pull dragged a fresh spill of precum onto Gareth’s fingers and down toward the mat.

“Listen to you,” Gareth said, voice rough with his own hard-on straining in his pants. “Grunting like livestock. That’s what you are tonight. My dairy cow. Built to be milked on your knees. Look at this cock, swollen, dripping, trying so hard to give. I’m going to pull every drop out of you and put it in that pail. You don’t come until I say the bucket’s ready. You just leak and take it.”

He sped the pulls, still long, still milking rather than jerking, squeezing harder at the base and twisting just under the head so Rupert’s thighs shook. The plug fucked in and out of his ass in time, a wet, obscene sound every time it seated. Rupert’s moans got louder, higher, wrecked. His cock pulsed in Gareth’s fist, precum running in a steady thread now, slicking Gareth’s wrist.

Gareth slapped his balls. Not cruel, sharp enough to make Rupert yelp and clench around the plug. “Louder. Cows don’t whimper. They moo when they’re being milked. Let me hear it.”

“Moo,” Rupert gasped, face burning, cock jumping in that relentless fist. Another slap, firmer, the sting blooming hot under his sac while the plug drove deep. “Moo—fuck—moo, please, I’m your cow, milk me, I’m gonna—”

“Louder.”

“Moooo,” Rupert cried, shameless, voice cracking as Gareth milked him in long, squeezing pulls and fucked the tail in and out of his ass. “Moooo, please, I’m dripping, I’m so full, milk your cow, take it all—”

Gareth dragged the metal pail under him with his knee, angling it beneath the hanging cock. “There. That’s your bucket. You give it here. Hands-free. You don’t touch. You just erupt for me like a good little dairy animal and fill it.”

He worked faster now, still those long milking strokes, root to tip, squeezing, releasing, squeezing, the plug pumping his hole in a dirty counter-rhythm. Rupert’s arms locked. His back bowed. The clamps tugged his nipples with every shudder. Balls drawing tight, cock swelling thicker in Gareth’s fist, he moaned and mooed and stayed obediently on all fours while Gareth used him like livestock.

“Give it,” Gareth demanded. “Squirt in the pail. Milk for me. Now.”

Rupert broke. The orgasm hit hands-free and vicious, ripped out of him by those relentless pulls and the plug grinding his prostate. His cock jerked in Gareth’s grip and the first powerful spurt shot into the metal pail with a wet ring against the bottom. Gareth aimed him and kept milking, long squeezing strokes that dragged the next thick rope out, then another, then another, hot and heavy, splattering the inside of the bucket. Rupert shouted, mooing through it, hips twitching but never leaving his hands and knees, ass clenching around the tail while Gareth tugged it and stroked him through every pulse. Spurt after spurt, messy and copious, Gareth directing all of it down into the pail until the streams shortened to thick drips and Rupert was shaking, emptied, still leaking into that fist.

Gareth didn’t stop until the last weak pulse had been squeezed out and shaken into the bucket. Rupert’s cock twitched, oversensitive and shining, and a final drop fell with a soft tick against the metal.

The pail was half full, cloudy and obscene. Gareth set it on the mat in front of Rupert’s face, close enough that the smell of his own spend rose hot into his nose. He reached under and popped the clamps free. Blood rushed back into the bitten nipples and Rupert yelped, arms buckling, still planted on all fours. Gareth’s palm dragged once down the sweat-slick line of his back, a handler’s pat more than a kindness, and he leaned in by Rupert’s ear.

“Good cow. Look at that. Half a pail. You produced so much for me. Eager little dairy slut, mooing and squirting on command. That’s what I keep you for.”

Rupert trembled with aftershocks, tail still seated, collar heavy, cock dripping the last of it onto the mat between his knees. Gareth nudged the pail closer until the rim touched Rupert’s mouth.

“Lick it. You promised. Taste what you gave me.”

Rupert lowered his head, still on all fours, and lapped. The first taste was bitter and thick and his. He moaned and took another, tongue dragging through the mess at the edge of the pail while his spent cock twitched and his ass clenched around the plug. Gareth watched, hard and unsmiling, one hand fisted in the collar so Rupert couldn’t lift his face.

“That’s it. Clean your bucket, cow. Get that tongue in your own load and swallow what you squirted. My good little milker, on his knees, eating his cream like the filthy animal he is.”

Rupert lapped again, greedy and shaking, cum smearing his lips and chin while Gareth held him down to the pail and made him drink.