The milkman always wrings twice

This story is a direct sequel to Don’t cry over spilled milk. If you haven’t read that story yet you might want to check it out before reading this one.

Warning: Can contain traces of cum.

Featured in this story: Logan (click for pictures)

“He did what?!” Manuel listened to Logan’s recount on his phone.

The 18 year old Jerk’n’Drain professional was standing outside the Milking Station, smoking a cigarette. The tall, muscular Latino was wearing his usual uniform: a pair of white pants and a white t-shirt that his most of the tattoos on his body and contrasted nicely with his deep tan.

“You’re talking about the Perfect Ten Prostate Stimulator”, Manuel said slowly. “Yeah, he must have taken it with him. It works pretty well when you stuff it really deep into---“ He paused. “Yeah, exactly.” He nodded. “How many loads did he… Oh, wow. Looks like he’s learned a lot from me…” He chuckled before turning serious again. “I’m sorry, that was inappropriate. And he made you shoot your load in your own mouth? … Uhuh … And she was watching the whole time? … Uhuh …”



Manuel had called Logan out of courtesy. He enjoyed his job at the Jerk’n’Drain Milking Station. He met a lot of people, and he was quite good at getting as much sperm out of their balls as possible, a fact that worked to the advantage of both Manuel and the guys who came to him for a good milking: They got a lot of money for their precious fluids, and Manuel got a nice bonus on top of his salary for consistently exceeding his daily quota.

Usually, Manuel didn’t socialize with the guys whose balls he drained at work. It was generally frowned upon when Jerk’n’Drain professionals interacted their sources outside the Milking Station. There had been a couple of incidents where milkmen (as the Jerk’n’Drain professionals called themselves when nobody was listening) had used their expertise on some of their sources for entirely private reasons. Manuel knew the rules, and the rules were clear: Milk them for all they’re worth and forget about them.

With Logan Kruger, things were a bit different for Manuel. He had milked his dick at the Milking Station a couple of weeks ago, extracting a couple of copious, creamy loads that earned Logan a healthy sum of money. On his way home, Manuel had found Logan in the parking lot. He had just been dumped by his girlfriend and he needed a bit of cheering up. Manuel had invited him for a beer.

When Logan hadn’t showed up for another milking session, Manuel had decided to call him. It turned out that Logan had an idea and needed his help.

“Yeah, I’ll see what I can do”, Manuel said glumly. “We’ll teach that asshole a lesson.”

***

Jackson was in a good mood when he entered the Jerk’n’Drain Milking station a couple of minutes before his shift began. The 18 year old changed into the white uniform, whistling happily. He closed his locker and walked through the halls of the Milking Station, mumbling the rehearsed lines that every Jerk’n’Drain professional knew by heart: “There are almost a hundred Jerk’n’Drain Milking Stations in the United States. We pride ourselves with delivering outstanding product while treating our sources withh the respect and the care that they deserve.  Jerk’n’Drain is a supplier for a lot of renowned pharmaceutical companies and cosmetics manufacturers around the world. Our extraordinarily high quality standards are unmatched, and we hold 75% of the global sperm market, making Jerk’n’Drain the number one sperm supplier worldwide. If it’s sperm it’s Jerk’n’Drain.”

In the hall, Jackson walked into Manuel. “Hey”, he said. He ran his hand through his dark hair and smiled. “What’s up?”

Manuel smiled back at him. “Nothing much.”

Jackson nodded. “Slow day?”

Manuel shrugged. “Yeah. Just a couple of our regulars.” He looked at his watch. “I have an hour till my next appointment.” He sighed.

Jackson leaned over the desk to look at his appointments. “Damn”, he mumbled. “I have nothing for two hours!” He looked at Manuel. “That’s gonna fuck up our quotas…”

Manuel sighed. “Yeah. Don’t worry though, there’s be days when you wish you had four arms to milk all the dicks that are waiting to spill their sperm.” He laughed.

Jackson joined in the laughter.

There was a moment of silence.

“So what are you going to do until your first appointment?” Jackson asked.

Manuel smiled. “Oh, I have a little project I’m working on.”

Jackson looked at him. “Oh.”

Manuel looked at his feet and waited. He had set the bait. Now he needed Jackson to take it. Otherwise he’d see through his plan. Jackson was a smart boy. Manuel looked up and saw the curiosity in Jackson’s face. Maybe he wasn’t smart enough…

“What is it?” Jackson said.

Manuel shrugged. “Just a little project.” He smiled. “You know, I’m always trying to find ways to improve my work.” He looked at Jackson. “Improve my quota, you know.” He chuckled. “It’s all about the money, right?”

Jackson’s eyes lit up. “Yeah”, he said. “Sure.” He paused. “Do you want me to help you?”

Manuel raised his eyebrows.

“You could explain it to me”, Jackson said. “And I can give you some feedback. It’s always good to have a second opinion, right?”

Manuel pretended to think for a moment.

“Come on, man”, Jackson said. “There’s nothing else we could do anyway.”

Manuel shrugged. “Alright. I’ll show you. See what you think.” He smiled. “You are right, maybe you can help me.” He turned on his heels and walked down the hall. “Follow me.”

Manuel led Jackson down the stairs and into a sparsely furnished room. The walls were white. In the middle of the room was one of the Jerk’n’Drain massage tables with strategically placed hole in the middle. Below was a wooden milking stool and a shelf that held all the equipment that the milkmen needed for their work.
“Voilà”, Manuel said and pointed at the table.

Jackson wasn’t able to hide his disappointment. “This is it?” he said slowly. “That’s just a standard milking table.” He looked at Manuel.

Manuel smiled. “No it isn’t.” He walked up to the table and pointed at the leather belts at every corner of the table. “You know how people usually get up after you’ve gooten a double or a triple load out of them, right?”

Jackson nodded slowly.

“Sometimes there’s another load left in their balls, right?” Manuel continued. “They just don’t know it.”

Jackson looked at Manuel. “So you tie them to the table, and…”

“…milk another load out of them before they know it”, Manuel smiled. “As soon as it’s over they’ll thank me for it. They get more money, too, right?”

“You have to be quick, though”, Jackson said. “Most people won’t like getting milked against their will.”

Manuel chuckled. “That’s why you’ll have to make sure they don’t scream”, he said, pointing at a ball gag at the top of the table.

Jackson’s face broke into a grin. “Nice.”

Manuel smiled. “Right?”

There was a small pause.

“So it’s ready, right?” Jackson said.

Manuel shook his head. “Not yet. I don’t know if the straps and the ball gag work, you know.”

Jackson grabbed one of the leather straps. “They look pretty solid.”

Manuel nodded. “Yeah – but you never know, right? I don’t want the source to jump off the table before I’m finished with him, right?”

Jackson examined the strap, nodding slowly.

Manuel waited.

“You know, let’s just try it”, Jackson suggested. “I’m pretty strong. Why don’t you tie me to the table and we’ll see if I can get out.”

Manuel raised his eyebrows, pretending to be surprised. “That’s a great idea!”

“See?” Jackson grinned. “I told you I could help you!”

Manuel grinned. “Yeah. Awesome.”

Jackson climbed onto the table and lay flat on his stomach.

Manuel walked up to him and scratched his head. He needed Jackson to get naked. He hadn’t been able to come up with a good reason. He cleared his throat.

“Yeah, I have to get naked, right?” Jackson interrupted him. “The clothes might make it easier to get out off the straps.”

Manuel raised his eyebrows. That was easy.

“See? I’m thinking of everything”, Jackson grinned. He jumped off the table and took off his clothes, stripping naked and revealing a nice, big cock and a fat pair of balls that was hanging low in his smooth sack.

Manuel chuckled and pointed at Jackson’s crotch. “You’d make a good source, you know that?”

Jackson grimaced and grabbed his big balls. “Yeah, those suckers are full to the brim. My girlfriend left me for her ex. Stupid bitch.” He looked and down and sighed. “I got a serious case of blue balls, man.”

Manuel grinned and made a milking gesture with his hands. “If you need any help…”

Jackson laughed. “No, thank you. I like to shoot my load the traditional way: on a hot chick’s bare tits.”

Manuel chuckled.

Jackson turned around and climbed onto the massage table again, letting his junk dangle through the hole. He spread and his arms and legs and put them into the leather straps. “Tie me up”, he said.

Manuel chuckled. “Alright”, he said and tied the first leather strap around Jackson’s left wrist.

“Tighter”, Jackson said. “We don’t want the poor guy to get away, right?” He let out a laugh.

Manuel grinned. “Yeah, we definitely don’t want that…”

“Imagine all the poor suckers”, Jackson chuckled while Manuel was tying his wrists and ankles to the massage table. “Lying there, their nuts exposed.” He lifted his head, looked at Manuel and grinned. “Those guys are so stupid. I bet they’ll just lie still while you tie them up.” He shook his head. “Stupid bastards.”

Manuel was finished. He stepped back and looked at Jackson. “So – how does it feel?”

Jackson tried moving his arms and legs. “Perfect”, he said. “I can’t move at all.”

Manuel nodded.

“Now put the gag in my mouth”, Jackson said.

Manuel grinned. “Sure.” He put the ball gag into Jackson’s mouth and tied it together behind his head.

He stepped back and smiled at Jackson. “How does it feel?”

Jackson tried to say something but all that came out was a muffled grunt.

Manuel chuckled. “Everything okay?”

Another muffled grunt.

“Perfect”, Manuel smiled. “Then we can start, right?”

Jackson laughed into his gag.

“Alright”, Manuel rubbed his hands and put on his rubber gloves. “Welcome to our Milking Station, sir. It’s your first time here, right?”

Jackson chuckled.

“Great”, Manuel smiled. “How many loads do you have for me today?”

Jackson replied with another muffled grunt, an amused expression in his eyes.

“Three?” Manuel feigned surprise. “That’s very generous of you, sir! You’ll make a lot of money today.”

Jackson let out a muffled laugh.

“And, who knows, maybe we’ll get a fourth load out of your balls”, Manuel winked at Jackson.

Jackson winked back at him.

The door opened and Logan entered the room.

Manuel looked at him and smiled. “We’re ready”, he said.

Jackson couldn’t turn his head far enough to see who had entered the room. He looked at Manuel with a quizzical expression on his face.

Manuel’s smile grew cold. “We have a visitor today. He’ll observe the procedure. I hope you don’t mind, sir.”

Logan walked up to Manuel and stood next to him. “Hey, Jackson”, he said calmly.

Jackson’s facial expression changed. He squirmed on the massage table, struggling to break free. But the leather straps held him firmly in place. A look of panic appeared on his face. His eyes were wide open and he tried to scream through his gag. Only muffled groans came out of his mouth.

“Take a seat”, Manuel said and motioned for Logan to sit down in front of the table. Manuel winked at Jackson and added, “This might take a little while.”

Jackson struggled against his restraints, grunting and groaning in protest.

Logan sat down on a chair and leaned back, a huge grin on his face.

Manuel took the wooden milking stool and sat down under the massage table.

Jackson’s junk was dangling right in front of his nose.

Logan looked Jackson in the eyes and smiled.

Jackson was struggling and floundering. Beads of sweat were running down his young, handsome face.

“Do you want me to use some lube?” Manuel asked politely.

Jackson screamed into his gag.

“No? Okay”, Manuel shrugged and grabbed Jackson’s limp dick. “You got a nice piece there, sir. If we do a triple without lube it might get a bit sore.” He paused, smiling when he heard Jackson’s muffled screams of protest. “You don’t care, sir? Alright. Don’t say I didn’t warn you…” Manuel looked at Logan and winked.

Logan chuckled.

Manuel grabbed Jackson’s fat cock and started jerking it roughly with his right hand. He balled his left fist and smashed it into Jackson’s tender nuts, making him wail into his gag.

Jackson looked at Logan, his face contorted in pain, a pleading expression in his eyes.

Logan just looked back at him and grinned.

Manuel whistled happily, jerking Jackson’s dick while pounding his gonads like a prize fighter. The sound of Manuel’s knuckles connecting with Jackson’s meaty testicles echoed through the room, mixing with Jackson’s muffled screams.

“I’ll get a nice, big load out of your nuts”, Manuel said. “That’s just what I need on a slow day like this.” He chuckled. “Thank you for that!”

Jackson screamed into his ball gag as Manuel’s fist smashed into his nuts.

“Ooooh”, Manuel grinned. “Looks like the first load is ready…” He threw a hard, mean punch into Jackson’s nuts before turning to Logan. “Could you fetch me the cup, please?”

“Sure”, Logan smiled. He got up, took a plastic cup and kneeled next to Manuel.

“Hold it for me, please”, Manuel said casually while continuing to punch Jackson’s fat lowhangers. He aimed Jackson’s dick at the cup just as the first spurt of jizz came out, splattering against the bottom of the cup.

Jackson let out a muffled wail.

Manuel chuckled. He stopped punching and grabbed Jackson’s right nut in a vise-like grip. He squeezed hard, then he focused his attention on Jackson’s left nut. Jerking his dick in long, even strokes, Manuel alternately squeezed Jackson’s left nut and his right nut to make sure that both of his testicles were properly drained.

Jet after jet of cum splashed into the cup.

It seemed like an endless orgasm.

Jackson was wailing and moaning, his face contorted in pain.

Manuel milked Jackson’s dick and balls until every drop of Jackson’s creamy load had found its way into the cup.

A satisfied smile on his face, Manuel skimmed the last drop from Jackson’s dickhead by scratching his fingernails over the sensitive surface.

Jackson let out a miserable moan.

Manuel smiled at Logan. “Okay, thanks. Put the cup on the ground, please. You can sit down. The second load will take a little while.”

Logan nodded and sat down in his chair. He looked at Jackson and smiled.

Jackson’s face was a mask of pain. His hair was wet with sweat and his eyes were glassy and filled with tears.

Manuel didn’t waste any time. He didn’t allow Jackson’s spent dick to go soft and continued jerking it. At the same time, he resumed punching his drained balls.

Five minutes later, Jackson came again. Another load, not as big as the first one but still rather impressive, joined its predecessor in the plastic cup while Manuel was expertly squeezing and kneading Jackson’s balls.

When the second orgasm was over, Manuel put a lid on the cup and placed it on the ground. He looked at Logan and smiled. “Wanna help me with the third one?”

Logan chuckled. “Sure.”

“Great”, Manuel said. “Get your chair over here and kick his balls while I jerk him.”

Logan grinned and did as he was told.

A moment later, Logan’s sneaker-clad foot smashed into Jackson’s sore, swollen nuts.

Jackson let out an anguished wail.

Manuel stroked Jackson’s erection with both of his hands, massaging the shaft at a steady pace, while Logan was sending kick after nut-smashing kick into Jackson’s dangling ballsack.

“You know”, Manuel said, raising his voice to drown out Jackson’s screams and groans, “kicking a load out is usually quite effective, especially when you’ve already drained a source’s balls a couple of times.”

Logan chuckled and kicked Jackson’s nuts hard, smashing them flat against the undersurface of the massage table.

Jackson’s voice cracked and he let out a shrill squeal.

“Good one”, Manuel smiled, nodding at Logan. He was jerking Jackson’s dick with both of his hands as if he was milking a cow. “The sperm quality suffers, though.”

Another kick smashed into Jackson’s balls, eliciting a high-pitched wail.

“If you kick it out, I mean”, Manuel added casually. “Lowers the sperm count, you know.”

Logan kicked Jackson’s balls again, making him shriek in agony.

“On the other hand it’s quicker than punching it out”, Manuel continued. “It’s like you’re telling the nuts: ‘Just give it up or you’ll get smashed to pieces.’” Manuel laughed while jerking Jackson’s dick. “See?” He reached down and grabbed a fresh cup, aiming Jackson’s dick at it while Logan continued kicking Jackson’s nuts as hard as he could.

Jackson’s third orgasm was violent and painful. Almost a dozen big, creamy spurts landed in the cup.

Logan continued kicking his nuts, trying to bust another couple of jets out, but Jackson’s twitching dick produced nothing but hot air.

“Okay”, Manuel said. “Looks like they’re empty.” He grabbed Jackson’s ballsack and examined his testicles. They were visibly swollen, the skin fiery red and covered in bruises. Manuel looked at Logan and grinned. “But I’m an expert, so…”

He winked at Logan and opened his mouth, wrapping his lips around Jackson’s spent cock. He squeezed and kneaded Jackson’s balls with both of his hands while sucking on his dick, humming some song that Logan knew from the radio.

Logan watched him, an amused his expression on his face.

Jackson’s voice had turned hoarse and raspy as he groaned and moaned into his gag.

Manuel’s fingertips dug deep into the soft, tender flesh of Jackson’s testicles while he was sucking his cock.

After more than five minutes of squeezing and sucking, Manuel let Jackson’s dick out of his mouth and wiped his mouth with the back of his hand. “Here we go”, he said with a smile and grabbed the cup, bringing it up to Jackson’s dick just in time.

This time, there were no jets or spurts. The cum dribbled out of Jackson’s dick and into the cup as if someone had turned on an old, clogged up faucet.

Manuel and Logan watched the milky liquid trickle into the cup.

Manuel smiled at Logan. “Looks like we are done, huh?”

Logan chuckled. “Yeah, thanks, man, that was---“

“Uh, uh, uh!” Manuel shook his head, raising his index finger. “I’m an expert, remember?” He chuckled and placed the cup on the ground. Jackson’s dick was still dripping, and his cum landed in the cup.

Manuel got up from his milking stool and stretched his limbs. He looked at Jackson’s ass and cracked his knuckles.

Logan grimaced.

“Stay seated”, Manuel said with a smile. “Just watch. Keep your eyes on the cup.” He winked at Logan. “I’ll show you what my magic fingers can do…”

Logan laughed.

Manuel spread Jackson’s ass cheeks and looked at his tight, puckered hole. “I bet you’re a virgin”, he chuckled, smacking Jackson’s ass with the palm of his hand.

Jackson let out a panicked grunt.

“Don’t worry, I’ll be gentle”, Manuel said. He looked at Logan, winked, and mouthed, “Not.”

Logan chuckled.

“Keep your eyes on the cup”, Manuel repeated before jabbing his index finger into Jackson’s hole, burying it deep inside.

Jackson let out a long, muffled scream.

Manuel wiggled his finger around until he found what he was looking for, and pressed his finger against Jackson’s prostate.

Logan let out a laugh. A new flow of cum came out of Jackson’s dick, landing in the cup.

“See?” Manuel chuckled. “Magic fingers.” He continued massaging Jackson’s prostate, coaxing more and more sperm out of his balls.

“The cup is almost full”, Logan said.

“There’s another one right there”, Manuel said. “Could you…?” He grinned. “I got my hands full.”

Logan chuckled and replaced the full cup with an empty one, making sure not to waste a drop.

“You can squeeze his balls if you feel like it”, Manuel said casually. “Take a pair of gloves.”

Logan found the gloves and wrapped his hands around Jackson’s balls, squeezing them with all the force he could muster while Manuel penetrated his hole with his finger.

A seemingly endless flow of cum trickled down into the cup.

After what seemed like an eternity, the flow stopped.

Manuel continued pressing his finger against Jackson’s prostate for another couple of minutes until he was sure that there was not a drop of cum left inside Jackson’s hole.

Then he pulled out his finger and knelt down next to Logan.

The two boys looked at Jackson’s balls.

They were swollen and bloated and covered in bruises.

Jackson was groaning and moaning miserably.

“I don’t think he’ll fuck your girl again”, Manuel grinned and patted Logan’s back. “Not this week, anyway…”

Logan looked at Manuel and nodded. “Thanks.”

Manuel shrugged. “Sure, anytime.”

Logan got up and stood in front of Jackson. He looked into Jackson’s pain-contorted, sweaty face. His eyes were red and teary.

Jackson let out a pitiful sob.

Without a word, Logan averted his gaze and walked towards the door.

Manuel cleared his throat. “Hey, about my---“

“Yeah”, Logan grimaced. “Yeah, sure.”

Manuel smiled. “Nice. Just go upstairs and take a table. I’ll be with you in a minute.” He thought for a moment. “You’ve been in chastity for…”

“A week”, Logan mumbled. “Since we talked.”

Manuel smiled. “Awesome. So we’re doing a triple, right?”

Logan nodded, absent-mindedly fumbling with his crotch. “A triple sounds fair.”

“Awesome”, Manuel repeated. “Just wait for me upstairs.”

Logan left the room.

Manuel got up and put a lid on the third cup. He stacked the cups on top of each other and placed them on the massage table before taking the gag out of Jackson’s mouth and untying the leather straps.

Jackson coughed.

“Listen, man”, Manuel said, putting his hand on Jackson’s naked, sweaty shoulder. “No offense, right? You deserved that and you know it, right?”

Jackson groaned and curled up in a ball, cupping his balls.

“As far as I’m concerned”, Manuel said, taking the stack of cups and balancing them with one hand while opening the door with the other, “everything is fine between us, right? Just don’t fuck another guy’s girl. Don’t do that, man. It’s not right.” He looked at Jackson for a moment. “Alright, see you later.” He smiled. “I’ve got a customer waiting…”