Don’t cry over spilled milk

Special thanks to Carter and Ibi who came up with the plot for this story.

Warning: Contains graphic homosexuality.

Featured in this story: Logan (click for pictures)

“See you tomorrow, Manuel”, Jackson said cheerfully. He put the white t-shirt and the white pants into his locker along with the white plastic apron. Whistling happily, he left the Jerk’n’Drain Milking Station and headed for his car.

The 18 year old high school student had been working as a Jerk’n’Drain professional for a couple of weeks. At first it had seemed odd, and he had made a lot of mistakes. But now he was really good at it. Today, in a single shift, he had relieved more than a dozen guys of their loads. He had been jerking dicks and busting balls like a pro. He was a power draining machine. He was one of the top harvesters in the station.  And he was on track to beat Manuel as employee of the month.

Jackson looked at his phone. One text message. That was probably Ashley. He read the message, expecting some dirty talk and maybe even a naughty picture. She had been insatiable lately, and Jackson loved it. Today, he had managed to sneak out a “Jerk’n’Drain Perfect Ten Prostate Stimulator” or – in the words of Manuel – “a big fucking dildo”. He was pretty sure that it would work on a girl, too. And he knew that Ashley would be willing to try it…



He read the message again.

It wasn’t Ashley. It was Logan, Ashley’s ex. “9 pm. BH gym. I’ll kick your ass. L.”

Jackson and Logan had a history.

A couple of months ago Logan had lost a bet to Jackson, and he had paid for it, naked and tied up in the locker room, leaving his ego and his balls badly bruised.

Then, a couple of weeks ago, on Jackson’s first day on the job at the Jerk’n’Drain Milking Station, Jackson had busted Logan’s balls and milked him dry.

In addition to that, Jackson had taken his girlfriend.

Somehow, Logan had taken all those things personally.

Jackson grinned. Apparently, Logan wanted a fight. No problem. He’d get it.

He sent a message with his phone and got into his car.

Half an hour later, he arrived at the Bartlet High gym. The parking lot was empty except for Logan’s car.

Jackson entered through the front door.

The gym was empty and dimly lit.

Jackson continued walking until he was standing in the middle of the gym. Suddenly he heard a voice.

“There you are.”

Jackson stopped and slowly turned around.

Logan was standing in front of it, dressed in his red wrestling singlet.

The two 18 year old guys looked at each other for a moment. It was like the climactic meeting between the hero and the bad guy in a Spaghetti Western. The only thing that was missing were cowboy hats. And an Ennio Morricone soundtrack.

“You took my girl”, Logan said.

Jackson let out a laugh. “That’s what this is about? Get over it, man!”

“You took Ashley from me”, Logan said.

Jackson shrugged. “You didn’t satisfy her – and now you’re blaming me? Come on. This is ridiculous!”

“I challenge you to a fight, mano a mano”, Logan said. “A wrestling match. The winner gets Ashley.”

Jackson chuckled. “Does she know about this? I don’t think she’d appreciate being treated like a trophy…”

“She doesn’t have to know”, Logan said. “If I win you’ll end it. And if you win I’ll be out of her life.”

Jackson laughed. “Man, you already are out of her life. This doesn’t look like a fair deal to me…”

The was a brief pause.

“Alright, let’s do it”, Jackson grinned and started taking his clothes off until he was wearing nothing but a skimpy pair of black briefs. When Jackson threw his jacket to the ground, the “Jerk’n’Drain Perfect Ten Prostate Stimulator” slipped out of the pocket and rolled towards Logan.

Logan’s eyes narrowed. Then his face broke into a grin. “You need that thing to satisfy her?”

Jackson ran his hand through his dark brown hair and grinned. “She likes to experiment. It doesn’t surprise me that you didn’t know. She told me how boring you are.” He chuckled and adjusted his crotch. “She’s very happy with what I have to offer.” He pulled down his underwear, revealing a big, soft dick and a pair of nice, low-hanging testicles.

Logan watched him.

“What?” Jackson chuckled and pulled his underwear up again. “Never seen a big dick before?” He grinned, flexing his muscles.

Logan was silence.

Jackson raised his eyebrows. “What? You frightened? Afraid I’ll defeat you?”

Logan let out an angry growl.

Then the handsome blond high school student started running, heading for Jackson. His face was contorted in anger. That guy had stolen his girl, had humiliated him, emasculated him in front of her. He was going to pay!

The past couple of weeks had been hell for Logan. He loved Ashley, really loved her. And he missed her terribly. They had been the perfect match. King and queen of Bartlet High. No other girl could ever give him what she had. No other girl could ever love him like she had. No other girl could ever make him feel the way she had. Jackson was going to pay!

Jackson had a smile on his face. Ashley had told him a lot about Logan. When they were in bed together, when his head was buried between her thighs. He seemed to be a decent guy. Under different circumstances, Jackson and him could have been friends. But things were like they were.

Logan jumped at Jackson, grunting angrily. His mind was focused on one thing: He had to get Ashley back.

Jackson took a step back and brought his knee up just in time for Logan to land on it crotch-first.

Logan’s nuts were squashed by his own weight and he let out a miserable groan. His eyes widened and he stared at Jackson for a brief moment before collapsing on the ground, moaning in pain and cupping his crotch.

Jackson sighed. He almost felt sorry for this guy. Almost.

“Got enough?” he smirked. “You know, maybe we should call it a night. I’ve got plans with Ashley. We wanted to go see a movie. But maybe we’ll just go to my place and fuck all night. Maybe we’ll have a go at some butt love tonight.”

Logan looked up at him, grimacing in pain and anger. With a low grunt, he brought up his fist and sent it crashing into the big, soft mound inside Jackson’s briefs, knocking the wind out of his lungs.

Jackson let out a surprised yelp.

Logan followed up with another hard uppercut that hit Jackson right in his nuts, making him scream from the top of his lungs.

“Try making butt love with these”, Logan growled.

Jackson doubled over in pain, clutching his crotch. “You little fucker”, he grunted, reaching inside his underwear and rubbing his balls. “You shouldn’t have done that.”

Logan got up, groaning and grimacing. “You shouldn’t have stolen my girl!”

The two boys looked at each other in silence.

Suddenly, Logan let out a growl and lunged at Jackson.

Jackson staggered back, landing on his back with Logan on top of him.

They grappled, each of them trying to get the upper hand. Logan sent his knee in between Jackson’s thighs, making him howl in pain. Jackson retaliated with a vicious knee of his own that connected perfectly with Logan’s balls which were held in place by his wrestling singlet.

The boys rolled around, squeezing each others’ nuts, hitting them and punching them, kneeing them, yanking and twisting them.

The gym was filled with grunts and groans as both of them tried hitting their opponent where it hurt.

Jackson and Logan were panting and moaning, their bodies glistening with sweat.

The physical activity didn’t fail to have an effect on both of them. They were 18 year old boys after all, and soon they were both sporting huge erections.

“You seem to enjoy this”, Jackson grunted, reaching inside Logan’s singlet and grabbing his hard dick by the shaft. “You really sure that this is about Ashley?”

“Fuck you”, Logan grunted, trying to get his own hands into Jackson’s underwear. But Jackson twisted his body, getting his precious jewels safely out of reach.

“I’m starting to think that you are hot for me”, Jackson chuckled. “Why didn’t you just ask me out on a date?” He wrapped his thighs around Logan’s lower legs and managed to hold his arms and his upper body down with his body weight.

“Fuck you”, Logan repeated, grunting and groaning, desperately trying to free himself.

Jackson grinned. It looked like this was a perfect chance to put his experience at work to good use… He started jerking Logan’s dick inside his singlet just like he had done more than a dozen times during today’s shift at the Jerk’n’Drain Milking Station.

Logan’s eyes opened wide when he figured out what Jackson was up to. “No!” he croaked.

“You wanna give up?” Jackson grinned, continuing to massage Logan’s dick. His palm was slick with precum and he gently ran his hand over the tip of Logan’s dick like a true Jerk’n’Drain professional.

“No way!” Logan shouted before inhaling sharply when Jackson moved his free hand into Logan’s singlet and wrapped his fingers tightly around Logan’s nuts.

“Wanna give up?” Jackson repeated with a mean grin.

“No way”, Logan whispered breathlessly while Jackson was gradually increasing the force, squishing Logan’s juicy nuts with his bare hand until Logan let out a whimpering moan.

“Alright”, Jackson chuckled.

A couple of quick, well-executed strokes later, Logan let out a deep, guttural moan and shot his load into his singlet.

Jackson let out a laugh and continued massaging Logan’s rock-hard dick while squeezing his contracting balls.

“Oh no”, Logan croaked as jet after jet of sticky spunk found its way into his wrestling singlet, creating a huge, wet spot that grew wider and wider with every new spurt of his throbbing cock.

“Wow, you sure worked up a load, my friend”, Jackson said with a derisive laugh. “Haven’t had sex for a while, huh?”

Logan was groaning and moaning, his body convulsing as Jackson’s expert hands milked his dick for all it was worth while squeezing every last drop of cum out of his busy balls.

Finally, Logan’s body relaxed and he closed his eyes with a defeated sigh, panting heavily. “You win”, Logan whispered in a toneless voice.

Jackson chuckled. “Yeah, I win.” His eyes fell on the “Jerk’n’Drain Perfect Ten Prostate Stimulator” and a mean grin spread on his face. “What do you think, loser, are you up for a little fun?”

Logan followed Jackson’s gaze and his eyes widened when he spotted the huge dildo. His face went white as ashes. “Oh no, you---“

Jackson interrupted him with a quick, hard punch to his drained, spent balls, making Logan scream in agony.

Before Logan had a chance to put up any resistance, Jackson threw Logan’s legs over his head and used his singlet to completely immobilize Logan. Within seconds, Logan’s arms were tied behind his back, his legs were crossed and tied behind his head, his knees almost touching his ears. Logan’s eyes were wide open in shock and horror.

“Wow, you’re flexible”, Jackson chuckled, ripping Logan’s singlet apart to expose his ass.

Logan’s chubby, recently drained dick flopped down, its head touching Logan’s lips.

“You bastard!” Logan whispered, his mouth involuntarily touching his dick, causing it to respond to the stimulation by growing slowly. Logan squinted at his cock. “Oh, fuck!” he yelled. “Get me the fuck out of this mrgphf…”

Jackson started laughing uncontrollably when he watched Logan’s dick entering Logan’s mouth and expanding in a way that turned it into a perfect gag.

Logan’s lips were spread around his own huge dick. His eyes filled with terror as Jackson reached for the dildo.

“Perfect”, Jackson laughed. He reached inside the shreds of Logan’s singlet and scooped up some of his cum before generously applying it to the big, fat dildo, coating the huge plastic tool with Logan’s sticky spunk.

“Now, Mr. Kruger”, Jackson said in a mock-friendly voice, drawing on hours of experience as a Jerk’n’Drain professional, “do you want me to stimulate your prostate?”

“Mgphghph!” Logan tried frantically to protest, but his own hard dick in his mouth made it impossible for him to articulate himself.

“Great, Mr. Kruger”, Jackson chuckled, slapping the cum-covered dildo on Logan’s hole a couple of times. “This is your first time, huh? Don’t worry, we’ll get this thing all the way into your tight little hole.”

Logan let out a guttural groan, his lips wrapped around his own dick. He felt his dick throb and realized that every time he tried to say something he was stimulating his own dick, basically giving himself a humming blowjob.

Jackson lined up the huge dildo with Logan’s hole and tried to slip it in. “You got a really tight hole, Mr. Kruger”, he singsonged with a mean grin. “Don’t worry. When we’re through with you, it’ll be nice and loose…”

Logan let out a frustrated howl.

“Now open wide, Mr. Kruger”, Jackson grinned, trying to force the dildo into Logan’s asshole.

In a desperate act of disobedience, Logan was clenching his hole shut with all the force he could muster.

Jackson sighed. “Okay, Mr. Kruger, let’s do it the hard way…” He lifted his hand, balled his fist and sent it crashing into Logan’s balls as hard as he could.

Logan let out a muffled scream as sharp, piercing pain radiated from his testicles while his dick was shoved further into his mouth.

That moment of distraction was enough for Jackson to enter Logan’s hole, shoving the dildo halfway into Logan’s ass and eliciting another muffled scream from Logan’s stuffed mouth.

“Here we go, Mr. Kruger”, Jackson laughed and started shoving the huge dildo in an out of Logan’s virgin hole.

Logan was whimpering and moaning, his own dick twitching and throbbing in his mouth while his asshole was stretched by Jackson’s forceful invasion.

“Look at your testicles, Mr. Kruger, I’m sure there’s another huge load in them that’s just dying to get out!” Jackson laughed, ramming the dildo all the way into Logan’s hole before grabbing Logan’s balls and trapping them at the bottom of their sack.

With a mean grin, Jackson started slapping Logan’s gonads with his palm, going harder and harder with every hit while the dildo was jammed deep inside Logan’s ass.

Soon, Logan’s balls were fiery red and considerably swollen.

Logan’s eyes were filled with tears and he just stared at Jackson who was having the time of his life, slapping and punching Logan’s hapless testicles.

“Oh, I think you’re close”, Jackson smiled, punching Logan’s balls hard at a steady rhythm. “They’re trying to pull up. Watch out, Mr. Kruger, here it comes!”

Logan’s eyes widened as his dick started twitching violently and shooting a big, creamy load of cum directly into his own mouth and down his throat. Logan choked on his own spunk before gulping it down to avoid drowning in his own juice.

Jackson was laughing his ass off, pounding away at Logan’s nuts as if he was trying to turn them into creamy nut butter, punching every last drop of cum out of his balls and down his throat.

Logan’s eyes were filled with tears as he swallowed his pent-up sperm while his nuts were bashed and his virgin hole was stretched to capacity by the oversized dildo.

Finally, Logan’s orgasm subsided and Jackson stopped punching his balls.

“Well done, Mr. Kruger”, Jackson said with a mean grin, grabbing Logan’s spent nuts and squeezing them hard. “These babies are completely empty now…” He pulled the dildo out of Logan’s ass, leaving his hole gaping open, sore and twitching.

Jackson looked at the dildo and chuckled. “Don’t you think it’s pretty funny that I’ll stuff this thing up Ashley’s pussy in an hour?”

Logan let out a miserable whimper.

Jackson grinned. “Maybe I’ll let her lick it first. Let her get her lips around this thing. Do you think she’ll recognize your taste? Do you want me to tell her where it has been?” He slapped the dildo on Logan’s gaping hole a couple of times. “Nah, let’s keep this a secret. Our sweet little secret. And if I---“

“What the fuck is going on?!” a loud female voice interrupted him.

Jackson froze. He slowly turned around, a sheepish grin on his face, positioning himself so she couldn’t see Logan. “Ashley”, he stammered. “Babe.” He lifted his arms and noticed he was holding the obscene dildo. He quickly brought it behind his back.

“What is going on?!” Ashley repeated.

Jackson smiled nervously. “Babe, I told you to--- I thought you’d wait for me outside in the---”

“I saw your car”, Ashley hissed. “Do you think I’m stupid?” She walked towards him. “I saw Logan’s car, too. Do you think you can have a little thing with him on the side?!”

Jackson shifted nervously, trying to hide Logan who was wrapped up in a neat little package on the ground behind his back.

“And I heard what you said”, Ashley said slowly. She raised her voice. “Logan, I know you’re hiding behind him. Come out.”

Logan let out a muffled whimper.

Ashley stepped to the side and saw him. Her eyes widened. She stared at Logan for a moment, taking in the sight of him tied up with his own wrestling singlet, his asshole exposed and gaping, his dick buried in his own mouth, his eyes filled with tears.

“Oh my god”, she whispered.

Jackson cleared his throat. “Listen, babe, I can explain.”

Ashley ignored him, staring at Logan in silence.

Logan closed his eyes, letting out a pitiful moan.

“He threatened you”, Jackson said. “He told me he’d beat you. I met him to talk some sense into him. But he ambushed me. He stripped me naked and tried to force me to have sex with him. Somehow I managed to fight back. It’s the truth, babe, I swear.”

Ashley slowly turned her head to look at him. “You tried to fight back with a dildo?” She let out a bitter laugh. “Liar. I heard you, remember? I heard what you said about me recognizing Logan’s taste and---“ She stopped. “Liar.”

Jackson shifted uncomfortably. “Babe, I---“

“Get out”, Ashley said.

Jackson bit his lower lip.

“Now”, Ashley said.

Jackson looked down at his feet. Then he picked up his clothes and left the gym.

Ashley turned to Logan and knelt down next to him. “I’m so sorry”, she whispered, gently running her hand over Logan’s face.

“Mgphghph.” Logan’s lips were still wrapped around his dick.

“I’m so sorry, Logan”, Ashley repeated. “I didn’t want this. I---“

“Mgphghph.” Logan repeated.

“Do you forgive me?” Ashley whispered.

Logan blinked. “Mgphghph.”

Ashley sighed.

There was a moment of silence.

 “Mgphghph.”

“I know, Logan, I know”, Ashley said.

Silence.

“You know, Logan”, Ashley said slowly. “I think I still love you.” She looked him in the eyes. “Do you still love me?”

Logan looked at her. “Mgphghph.”

Ashley smiled at him. “Oh, Logan, I’m so glad…”