Jake showed up at the old dairy farm looking for work and ended up stripped, roped, and strapped to the milking bench before the sun went down. The barn smelled like hay, sweat, and warm cow shit. Thick ropes circled his wrists and pulled his arms straight out to the sides. More rope around his chest and waist kept him flat on his belly on the padded table. His legs were spread wide and cuffed to the corners, ass up, balls hanging low between his thighs.
"You said you wanted the full experience," the farmer growled behind him. His name was Rick, forty-something, built like he lifted hay bales all day. He grabbed Jake's balls and gave them a firm squeeze. "This is it."
Rick wrapped a wide leather strap around the base of Jake's cock and balls, cinching it tight so everything stood out and swelled fast. Jake's dick thickened against the wood. Rick didn't waste time. He grabbed a clear plastic milking cup from the shelf, the kind they used on the cows but smaller, fitted with soft rubber seals. He smeared lube around the rim and shoved it over Jake's cockhead, pushing until the whole shaft disappeared inside. The suction kicked on with a low hum.
"Fuck," Jake grunted. The machine started pulsing right away, strong pulls that dragged at his cock like a hungry mouth. His balls tightened against the strap. Rick watched for a second, then walked around and slapped a heavy hand on Jake's ass.
"Keep breathing. It's gonna drain you dry."
The pump worked in steady cycles, suck, release, suck, release. Every pull made Jake's cock throb harder. Pre-cum leaked out and got sucked away immediately. Rick didn't touch him gently. He shoved two thick fingers into Jake's hole without warning, working them in deep and twisting. Jake pushed back as much as the ropes allowed. The machine kept pumping. His cock felt huge inside the cup, veins standing out, head swollen from the constant suction.
Rick pulled his fingers out and wiped them on Jake's thigh. He stepped away and came back with a different attachment, a smaller cup that fit over just the head and balls. He swapped it out quick, the new suction hitting harder and tighter. Jake groaned loud. His nuts ached from the strap and the relentless pull.
"Look at that cock leak," Rick said, voice low and rough. "Fucking farm slut. You came here to get milked like one of the herd."
He reached under and rolled Jake's balls in his palm, tugging them down while the machine worked the shaft. Jake's hips tried to buck but the ropes held him flat. Sweat ran down his back. The pump changed rhythm, longer sucks now, drawing his cock out and letting it slap back. Every time it released, Rick gave his balls a sharp slap that made them swing.
Jake's first load hit without warning. His cock jerked inside the cup and shot hard. The machine kept sucking, pulling the cum straight out and into the collection jar. Rick didn't stop. He left the pump running and walked around to Jake's head.
"Open," he ordered. Jake opened his mouth and Rick shoved his own thick cock between his lips. Jake sucked it sloppy while the machine kept working his spent dick. Rick fucked his throat in short thrusts, one hand gripping Jake's hair.
"Swallow it all when I give it to you," Rick said. "You're not done yet."
The machine switched to a faster pulse. Jake's cock, still sensitive, started swelling again inside the cup. Rick pulled out of his mouth and moved back behind him. He greased up a thick rubber plug and worked it into Jake's ass, twisting it until it sat deep. Then he turned on the vibrator built into the base.

The buzz traveled straight to Jake's prostate while the milking cup kept sucking.
Jake came again fifteen minutes later, shooting thinner this time but the machine didn't care. It kept pumping, draining every drop. Rick pulled the plug out and replaced it with his cock, fucking Jake in hard strokes that shoved him forward against the ropes. The milking cup stayed locked on, sucking through the whole fuck. Rick came deep in Jake's ass with a grunt, then pulled out and left the cum leaking down his thighs.
He swapped the cup again for a new one that covered cock and balls together. The suction started even stronger. Jake's third orgasm took longer, his body shaking against the ropes, cock raw and over-sensitive, but the machine forced it out anyway. Rick watched the jar fill, then turned the pump off and left it attached while he untied the chest ropes.
"Stay there," he said. "We'll do another round after you rest."
Jake lay there panting, cock still trapped in the cup, ass dripping, ropes still holding his legs spread. The barn was quiet except for the sound of his breathing. Rick came back with a bottle of water and held it to his lips.
"Drink. We're not finished milking you yet."