The Milking Den Ch. 03: Chase

"Hey! Is your spare room still free? I'm flying in for work next week and need a place to crash."

Chase's text sends a warm tingle down my body. I haven't heard from him since he left to take up a new position in another city.

"For you? Always." My fingers fly across my phone's screen.

"Sweet, thanks!"

Right afterwards, I see Chase typing a second message that takes a bit longer to write. Then a pause. He starts, he stops again.

I stare at my screen now, waiting for the weight to land. Is he thinking what I think he is?

Time stretches out like it does for a sub blindfolded.

***

I don't often rent out my spare room because I enjoy my private space very much. Chase, though, was different.

Twenty-six years old and working in the advertising industry, Chase had what I can only describe as big corgi energy - an infectious, sunlike aura that was light and warm all around. He was a real joy to house. Clean, bought snacks every now and then, no problems with payment at all. Most importantly, he agreed easily to my requirements. He nodded eagerly when I told him that I have regular visitors, and that the room down the corridor was out of bounds.

But by the sixth month of his tenancy, two new factors had emerged.

First, Chase's company was going through some hard times. Competitors were popping up all around, and gigs rolled in a bit slower for him. Rent started to come in a few days late; a few more months in and it started to come in instalments. Still, even though Chase's smile never waned, I could see that paying late really embarrassed him. "I'll pay you next week, promise! Sorry 'bout it, man." But who could get mad at him with that charming grin?

Second, and more interestingly, Chase seemed to be developing some inkling of what went on inside that room.

I don't think it took long for him to realise, on the nights that he came home during one of my sessions, that I was having people over for sexy gay recreation. On more than one occasion, he's also seen my boys enter all tough and mighty only to crawl out broken and blissed-out wrecks. He eyes them from the couch as they shuffle out; then, he turns back to me, smiles faintly in what I can only say is a knowing and impressed manner, then turns back to the television, which was probably never loud enough to drown out the roars from my den. I think this stoked both his curiosity and something else too. A strapping lad living alone in a big city, no girlfriend, a tightening career; unscratched was his urge to be regarded as beautiful.

That's probably why Chase started walking around the house in just his underwear.

The first time he pulled that stunt, my eyes nearly popped out into my coffee.

"Hey, buddy," Chase chirped as he swung into the kitchen headed for the fridge. Hair ruffled, slow easy stroll, rocking a tight pair of grey boxer briefs that revealed more than it hid.

Did I say "wow" out loud?

Either way, I'm sure I couldn't help but stare.

Chase is one of those guys who doesn't actually look buff until you see him with his clothes off. And when that happens, like on that sweet Saturday morning... what a sight to behold. Underneath that shirt, Chase was packing some respectable muscle, but not so big that he hulks out like my other boy Lawyer Dan. Instead, Chase is a buff pup. His shoulders, pecs and biceps are firm and claspable. And down there, inside those tight grey trunks that hugged his cheeks and thighs, a heavy bulge that swung with each step.

Chase winked at me as he ambled towards the fridge. I caught a whiff of his fresh scent, accompanied by a front row seat to the grand display of his ass. Snapping out of my sexed out stare, I tried turning my attention very conspicuously towards my coffee.

"Stop it! You're becoming a creepy live-in landlord!"

But inside my mind, I was entranced. That wink - was that Chase being Chase, as cheerful and stupidly charming as usual, or was that something more? This couldn't be, I told myself. I was reading my own thirst into this; guys walk about in their underwear all the time.

But then, my question was answered. Chase stood right there, stirring his mug in just his underwear, his beautiful sunkissed body on full display, his big bulge hanging ripe.

"How's it going, man?"

This big tease. Dumbly, I took a sip of my own steaming coffee. I remained barely in control of my eyes and that growing urge inside my pants.

And soon after that, after I revealed my weakness, Chase started tempting me more and more.

Underwear Chase became a frequent sight at home. For no reason at all, Chase would lounge about the apartment practically naked. Watching TV. Working at the kitchen table. And sluttiest of all - doing pushups, squats and crunches in nothing but his tight sweaty briefs. And he was enjoying it; that knowing smile became more of a smirk as I visibly struggled with the heat he stoked in me. Chase had become a visual feast of abs, pecs and bulge. There and then, I wanted to drag him into my den, tie him down to my table and punish him hard for being such a cocky straight boy.

But that would be letting Chase win. And you know me. I only do it when they want to surrender.

My chance came once rent season rolled around again.

"Chase, can we chat about this?"

Today, for a bit of variety, Chase was actually partially clothed. He was wearing a baggy tank top cut to show some shoulders and a flash of chest, probably because he wanted to leverage on his body to ease my nerves while being modest for our discussion. We sat at the kitchen table. His eyes were wide open like a begging puppy.

"You've been a great tenant, but this is the fourth month rent is coming in late."

Chase chuckles nervously. "I'm sorry, man. Work hasn't been easy. I promise, I'll get it in once my client pays us!" He offers me a tiny smile and a small shrug.

I knew that look for what it was. Chase was a deer lost in the woods. Now, it was my turn to smirk.

"Well. Why don't we negotiate?"

I had him where I needed. I leaned in and across the table.

"I think you have some idea of what I like doing with my guests. I think, also, that you might be interested. Why don't we make a deal?"

Chase looks stunned. How the tables have turned; my voice deepened as I corner him in my hunting ground.

"Clear your Saturday. I'll put you through a session, and in return I'll write off your rent for the month."

Chase is overwhelmed. My boys' strangled howls rumble in his mind. He seems to grapple with the consequences of his chronic thirst trapping. But he's considering it. Money is money, his eyes say as he pulls them back into himself. And then, as he opens up again, he glances back at me like a curious puppy. And, behind that initial shock, I can see that he wants this too. He licks his lips and shifts in his seat, as though making space down there to let something grow bigger.

"What do you mean by session?" He's practically getting hard in his eyes. He thinks this game is one he can swing to his side.

"Do you know what milking is?"

Five minutes later, we shake hands.

***

Ten o' clock. Chase emerges from his room fully clothed. He's wearing sleeves! Maybe he's getting cold feet, but the idea of lifting a thousand bucks off his shoulders sounds enticing enough for him to get naked for me. He's walking with his tail between his legs. He's tamed and timid now, but it'll be the experience on my bed that will break him. All these boys who think they're the ones in charge always get such a rude shock when they're all ruined and begging for mercy.

"Still up for this?" I ask as my hand reaches for the door knob.

Chase draws a quick breath. "Yep!" He lets out his tension with a chuckle. He puffs up his chest but I can sense a bit of fear inside. Now, I know he's exchanging his cum for money, but that doesn't mean he has to hate this. I give his arm a quick light smack.

"If you really need to quit, just say so. It's just two guys having fun."

Some very expensive, very wet fun. Reassured, Chase nods again, and the door to hell opens before him.

Chase's eyes widen like two full moons. "Oh, wow." In front of him is a big bondage bed with four posts and cuffs at each corner. To its side, a table lined with instruments for extracting every drop of him.

I pat the bed and strip him with my eyes. I've dreamed of payback for so long.

"Well, you seemed really happy to tease me with your body. Why stop now? Get naked." My words are soft and slick like a tongue licking his neck. It takes all my willpower to not reach down and grope myself as Chase obediently strips for me. His body is so proud of itself, thick and lean like a wolf in its prime. Soon, he shimmies down to his underwear - tight cyan boxer briefs that hug his package like a loving hand.

Chase looks at me sheepishly. He's always held the power, been the one to entrain the eye. This is his first time stripping at someone's command, revealing his body for another person's pleasure. Now, he's just one strap away from his dignity. Pleading.

I raise an eyebrow.

"Bro, your rent's not gonna pay itself."

Chase chuckles and sighs at the same time. He tucks his thumbs into his elastic band and pulls it down to reveal a big thick cock that's just asking to be edged. What graspble size; such huge balls. Looks like he took my advice to hold off from orgasming until we met for debt collection.

"Oh, man. That's a beautiful cock," I marvel. Chase chuckles and some of his studly confidence comes back.

"Like what you see?" He quips. Heat seems to radiate off his torso.

"Be careful what you ask, boy. Now, climb on and let's go."

Strapped down, his whole body pulled open and defenceless, Chase looks so much more impressive from a torturer's point of view. His delicate eyes and tousled hair, combined with that muscled body, makes him look so ruinable.

Standing by his side and gazing down at him, I start reading out our contract.

"Okay, big boy. Here's the deal. I'm going to jerk you off, and your job is to not cum. For each hour you hold your load in, I'll write off twenty percent of your rent. You get to cum at the end of each hour and walk away with that discount, so hold it in until the fifth hour and you'll get all your rent waived. But if you cum without permission at any time - even after you pass each hour - I'll charge you the full amount. Deal?"

Chase gulps as the gravity of the task becomes clear to him. Five hours of

selling his body and cum in exchange for money? He felt so used and degraded and the game hadn't even started yet. But he needed this; he needed to free up his wallet and he'd do whatever it takes.

"Yes. Deal."

Resigned, Chase grits his teeth and braces his abs for a good long day of clenching.

"Good." I grab my lube bottle. "Time to help myself to the buffet."

I squeezed a stream of lube all over his chest and abs like syrup over pancakes.

Chase blanches. That's how he's feeling now: exploited, sexualized. Objectifed.

"Chase, Chase, Chase. Whenever you paraded your body, did you ever think you'd end up like this? Naked and used by your landlord?"

As Chase recoiled at the touch of that cool liquid, I gloated over how much fun it would be to destroy him. His big brown eyes winced and seemed to plead for mercy - but I hadn't even started! As I slide my hand up his abs, gliding against their sculpted contours, Chase gasps hard. He trembles as I spread the lube out over his body, rubbing him all over like meat to be marinated, and then yelps as I find my way to his nipples. Flicking one and rubbing slowly against the other, I laugh at his agony.

"Answer my question, boy." Not in a dark evil dom way, but a stronger dude laughing at a friend who lost a bet. Chase starts giggling.

"No." He winces.

"No, sir." I pinch his nipples and twist them hard, and he yelps before breaking into even more laughter.

"You're gonna get it so, so bad. And remember - don't cum."

I swivel one hand up his hard cock and Chase already knows he's losing.

"Hour one starts now."

Each one of my boys reacts to my hands differently. Lawyer Dan is a stoic sufferer; Swimmer Scott is a shy shiverer. Chase here is a giggler. He chortles as he thrusts up into my hands. "Oh, yeah, I'm ready." His strong brows arch and his loins flare with heat.

Cruelly, I pull my hands off and leave him thrusting into nothing as he makes little yelps of need. "Dude, come on. It's only been twenty minutes." I rest my slippery hands on his thighs.

"Wait, what?" Chase shoots in disbelief. I see the world sink in his eyes; he was realising, too late down the road, that this was a trial by molten fire.

"Yeah. Do you want your rent cleared or not?"

"Ye... yes." Chase gulps and pulls himself up.

"Yes who?" I test, grabbing his dick and giving it a few quick pumps, almost pushing him over the brink for his rudeness.

"Oh, ah - yes, sir!"

"Good. Be strong, boy. You can do it. You're a tough straight boy, aren't you?"

For the next thirty-nine minutes, Chase thrashes and twists about on the bed as my hands jerk, rub and corkscrew around his dick endlessly. He screams and groans, but most endearingly - he laughs. I laugh in response as well as he gasps and pulls away, hustling and thrusting hard for his pay. It was so good to see that he was also having fun.

Fifty-nine minutes.

"Alright, buddy. That's the first hour. Do you wanna cum now and take twenty percent off?"

Chase looked like a squeezed out paint tube. Thoroughly dishevelled, coated thick with lube and sweat. I could see that struggle in his eyes between his will and his sex drive. His body stretched tight like a rope in tug of war.

Silence. Sweat drips down his broken brow.

"Alright then. I'll let you cum now."

Methodically, I pump away at his swollen dick. For a second, Chase's face relaxes in pleasure, ready to give in, but his conscience seizes him and he clamps back into action.

"Wait, stop!"

My hands pause midway down.

"I'll... I'll keep going. I wanna get it all." He said bravely, even though doubt lingers in the corner of his eyes.

"You sure?"

He gulps and nods.

"Remember - if you cum without permission you get nothing." I have to say this for his own good. He's so tender and ripe. I don't think he'll make it.

"Yes. I'm sure."

Never doubt the resolve of a straight boy proving his cock's worth.

Well, it's his funeral. I grin like a frat boy about to give his pledge a good time. "Happy to oblige."

Somehow, Chase makes it past hour two. But this time, he's a snivelling, weeping and convulsing wreck. Lying there covered shamefully in even more lube and foaming at the mouth with pain, I knew he wouldn't last much longer. From the way his cock throbbed with each touch and leaped with each stroke, it was clear he was just one inch away from bursting the biggest load of his life.

I had to get him now. Reach into his decimated mind and grab onto his brain to wring it dry.

"You've done so well, Chase. So much better than I expected." Chase grimaces and writhes on the bed, looking anything but victorious. He looks like a tortured prisoner.

"I'll make you an offer."

Chase raises his head as much as his restraints allow. His face is a mix of desperation and curiosity.

"I'll let you take all your rent back right now... but only if I stop without letting you cum. We pack up and you walk away with a full wallet and full balls."

Instantly, Chase dissolves into a mess of sighs and groaning noises. It's the sound of a man totally broken and reduced to the raw essence of his sex and dignity. He whimpers and actually really sobs. Imagine almost three hours of holding your body right on the edge of hell's peak... only to be told your final way out is to deny your primal urge. Pure mental torture.

And here's where I fuck his mind so deep he becomes my bitch for life.

"Or. I give you eighty percent off and let you cum right now."

Chase shuts up. He's listening; that's two hours more than he's earned. But what's the catch?

"But I'll milk you until there's absolutely nothing left inside your balls."

It's an easy choice. Without even considering the pain involved in his decision, Chase shoots right to the latter.

"I want to cum. Please. I just want to cum. I'll do anything to cum." Chase mumbles feverishly, pulls weakly at his restraints. His mind is barely conscious, floating between this world and the next.

Bingo. I make a big show of gratuitously lubing up my already slippery hands even further. "Chase, Chase, Chase. I hope you'll enjoy this as much as I do."

I edge him a little bit more just to make sure he's totally gone - my fists screw around his cock in different directions until I feel his prostate swell to the point of no return. Two hours and fifty minutes of pure sensual torture.

Chase is finally totally gone. His eyes are zoomed out and he's lost his power of speech. Now, dripping out limply onto the bed, he just moans and groans as his abs and arms spasm in time to my rhythm. Time for reaping my reward. I zoom in on his cock and swollen balls.

"This is it, buddy. You earned it. Cum, cum!" I switch to a standard single hand grip and pick up the pace, and Chase growls deep and strong like a charging bull. His hips buck and shoot like a rollicking cannon and his voice claws up to a big scream.

"Argh, oh, yes! YES, YES!"

And Chase roars, stabbed with a sword of hot gay pleasure.

Our stud blows a big load, and he does it gloriously. Big wet bursts soak us both with the sweetness of his cum, shots popping up so high they streak through my hair. Chase rocks and crashes repeatedly, again and again, warm lashes coursing across his muscles and tearing his pelvis apart with the sheer force of his orgasm. Never before have I seen a man so totally spent, fully drained, splattered with the liquid of his shame.

"Oh, my god."

A whole minute later, Chase emerges from his trance. His eyes are still misted over with the aftershock of that explosion.

I wait for his ass to land back on earth. And then, once sense returns to him, enough to register that hell lasts forever, I pick up his dick and jerk it again.

"I think there's more." The cruelest sentence a milker can use.

Chase's abs snap like a snakebite, trying futilely to protect his tender body from me, but my ropes bind him down hard, defenceless against my hands. He has a seizure of sensations as my fingers squeeze and jerk, rubbing evilly and relentlessly over his cock head as I rub and press down on his taint.

"No, there isn't! Please, stop... argh!!!" he laughs and begs. He's laughing so hard he's crying. His muscles spasm uselessly, too weak to resist but in too much pain to not. From his cock, I wreck his entire being.

"That was the deal, bro. I get to milk you dry. Man up and take it." Chase screams himself hoarse as I pump and pump and pump. "And I certainly think there's more."

Drunk on his suffering, I climb up onto his fractured body, straddling his trembling wet thighs to devote myself fully to the draining of my exhibitionistic slutty tenant. I gorge my hands on his chest and nipples, and I don't stop pumping until he's an inch away from fainting. He surrenders two more loads in the next hour and finally cums dry once more just as the sun sets.

Chase crawls out of the den on all fours, his muscles wasted, his entire body dripping wet and stinking of cum. That chain of four orgasms exhausted his manhood so badly it felt as though a hole had been drilled into his loins. He doesn't emerge from his room for the next day.

Two months later, Chase held off on his rent again, and he resumed doing pushups in his underwear.

***

It takes a while, a slow weighted pause, before his next message comes in.

"How do you want your rent?"