The Milking Den Ch. 09: Chase Meets Max

Chase and Max's beautiful, perfect bodies gleam on the couch. They stare at me, seated on a chair across them, like bunnies about to be devoured by a wolf.

I lean forward, sinking my elbows into my knees. We'd worked so hard to make today happen and I wanted everyone to have a good, wet time.

"Boys. The two of you will become very, very good friends today."

Chase and Max's oiled arms slide against each other.

"You will be edged until you cry. You will be totally used inside out."

"But only one of you will get to cum and enjoy it."

Chase and Max's eyes widen. I imagine their jaws would drop if they weren't strapped snugly closed with my ball gags. They glance at each other, whimpers catching in their throats. The reality of their predicament hits them: these boys are trapped in straight hell. Bound side by side with another nearly naked man, their thighs open, their bodies spread out for feasting. The only way out is to lean - physically and metaphorically - on each other.

And they signed up for this. Behind their outward terror, a dark and sweet longing unfolded inside their loins.

Chase and Max tremble as I waltz up to them. Time slows down in the long seconds that I take to cover this short distance. Mounting my prized stallions, I straddle their thick thighs, rubbing my thumbs on their bulges like ripe fruit. Against their manly self-restraint, my hands erode their pride and coax out soft, hushed moans. They dread how I'll torture them, but they love that I make them ache so good.

"Who will the lucky fucker be?"

***

Chase is no stranger to you and me. He was my roommate for a while and had some issues with rent, so we had to figure out a payment plan that both of us enjoyed (The Milking Den Chapter 3). He then came back for a bit and stayed with me again, and we also had a lot of fun milking him in exchange for cash (Chapters 6 and 7). Now, he's back visiting family and friends, and we just had to meet once more.

After all, I let him cum the last time - after being edged, objectified and used for a whole week - on the condition that we play with another one of my boys.

Chase had been hinting at it for a while too. In fact, he was the one who sparked off the topic. He kept dropping references about wondering how he stacked up against other men, and the way his cock stiffened in my hands when I mentioned it last milking was proof.

Max, too, is a bicurious muscle stud that wants to be worshipped. Last time, the personal trainer hit me up for a final hurrah to singlehood before getting married. Seems like the pleasure of being praised with word, hand and tongue was too sweet to resist. He's here for a "private coaching appointment".

Chase and Max moan softly, as if reluctant to intrude upon the straight space of their fellow prisoner, as I knead their full and thickening bulges. Chase looks up at the ceiling and Max down at his crotch, their gazes avoiding each other like repelling magnets.

"Come on, boys. You've already touched each other all over just now." Chase sniffles. "Oh, wait - almost all of each other. Why stop now? You have so much to learn about each other."

Max blushes a deep, potent red, intent on keeping his eyes off Chase.

"Do you boys want me to take your briefs off? Play with your cocks instead?"

Chase sniffles and manages a "yes" over his gag, and Max nods as his face tries not to crumble. My groping gets harder and stronger and both sets of hard, chocolate bar abs contract with longing.

"I'll do it if you look at each other."

Chase begs me with his puppy dog eyes and Max scrunches his face up in agony. This is torture for the hetero ego - it's one thing to play captive straight boy with me, but to acknowledge that they're lying side to side with another naked man?

"Come on, boys. Here, let me help you."

My hands trail up from their bulges, sliding up their well oiled torsos to cradle their heads and turn them towards each other. Chase's face quivers anxiously and Max's eyes crack open with bitter acceptance. They share a poignant, pained glance, powerless to resist the stripping, denuding and total milking of their bodies and minds.

"Good boys. Now, who's gonna get edged first?"

Max is the first to crack. He shuts his eyes in denial and makes a soft howling sound.

That's my cue - it's always more enjoyable to break the tough ones first. I pull Max's snug blue briefs down to let his cock spring up happily. He might be doing his whole reluctant macho thing, but his dick is saying something else.

***

"Hey guys!" Max and Chase flash their winning smiles as I let them both into the Zoom room, but they both look a bit too formal as they meet each other for the first time. Which is to be expected, right? It's not everyday you have a Zoom call with another straight-curious guy because you're planning a milking date at a friend's.

"Sup?" Chase grins, and Max waves back.

"How's your dog?" I ask Chase, who told me about his pet the last time he came over for his week-long torture marathon.

"Aww, you remembered! He's great, thanks!" Chase beams, a stiff weight releasing itself from his shoulders.

"That's awesome! Yeah, so, shall we get started?" I respond, glad they're both settling in. "Chase, Max. Max, Chase. Both of you told me you'd like to play with another guy, and I thought you'd be a good match for each other. I wanted to meet together so we could get to know each other, and maybe talk about what you want the session to look like. Chase, do you wanna start?"

"Yeah, sure!" I can see Chase lying back on his bed, holding his phone above him. "This was my idea, so, haha." Chase ruffles his bedhead hair. "Yeah, I guess I've always been kinda interested in being captured and tortured?"

"And you like it when your captor forces you to perform, right?" I suggest, and Chase chuckles as he blushes. He does! He loves it when I make him flaunt his muscles and fuck for me. "Max, are you into this too?"

"Yeah, in a sense," Max joins in, his eyes pointed upwards thoughtfully. "I'm a sportsperson, right? I've always wanted to be forced to compete sexually against another guy. It's just different, you know? When it's a man? You just feel like you can go all out and push, and not hold back!"

"Yeah, I get you, man!" Chase chips in.

"I'm so glad the two of you get along!" I gush, and Chase and Max whoop along. "I guess we're doing this, then!"

***

I text them later on Monday.

"Hey boys.

We're meeting this Saturday. Report at 2pm. We will be done by 10pm.

No cumming from now till then. You know I'll know.

Report in tight briefs.

Douche first."

***

Society demands a lot from men. Being powerful, confident, brave is not negotiable - men need to be this way or they are judged as weak. Chase and Max, and so many of my boys, are like that. Influential people in business and leaders of families, they invest so much energy into keeping up this facade of strength.

That's why Chase and Max keep coming back. I give them this space to be unapologetically vulnerable. To beg, moan and weep as I torture them with pleasure.

"Hey, man! How've you been?" I greet Max with a huge hug. He looks radiant and joyful. Married life is treating him well!

"Max, this is Chase." I gesture over to Chase sitting with a glass of water in my kitchen. Chase got here ten minutes earlier and we had been chatting about our jobs and work. Chase rises and nods at Max with a bright grin.

"Sup, man," Chase and Max greet each other with a good handshake. As they approach each other, I can sense the heat deepen in the room. It's like when opposing sports teams meet to exchange handshakes in the middle of the court - it's part brotherhood, part courtesy, but also smoky and slightly warm. I can see them testing the other's strength in their hands.

And it's time to get the ball rolling.

"Both of y'all good to go?" I ask, rubbing my hands. "Again, we're just having fun. If you need to stop, just say the word 'sunflower' and we'll stop. Do we want to go ahead?"

That final reckoning flashes past in their eyes. That's how it usually is with my boys. There's a moment of preemptive regret as they know they are giving themselves over to my devious hands. But then, that's exactly why they're here.

Chase and Max both nod, and I can see them stiffening.

"Great. Strip."

Straight men need release, no matter how momentary these windows might be, from the stress of being constantly strong.

Straight studs also secretly want to worship each other.

You know that old joke about how gym bros appreciate each other's muscles more than women do? That's absolutely true in my experience. Only another man understands the dedication, and can express that appreciation.

That's absolutely true for Chase and Max. Standing in their underwear, they steal glances at each other's fine sculpted bodies. Max is more of a conventional muscle jock, thick and broad, whereas Chase is a leaner, tighter pup. Down there, both of them are gifted. Chase is in a basic grey trunk, and Max is in something blue and bulging. Both of them are beautiful boys who want to get their hands on each other's beauty.

"You can just stare at each other, guys," I quip. "You're already here." Chase and Max laugh nervously, although that tension dissolves as they give themselves the permission to admire each other.

"Nice chest, bro," Chase comments, and Max giggles.

"It's nice, isn't it?" I ask, strolling over to a table and pulling out two bottles of thick massage oil. "Wouldn't you like to oil it up?"

Chase's jaw drops slightly, but he recovers and bites his lip. He looks at Max and blushes a deep red. Max, too, turns bright pink at the idea. I hold up the two palm-sized glass bottles to them.

"This is the warm-up, guys. Oil each other up. Everywhere. Use everything."

And then I sink into my couch, legs spread wide open, as I watch the show.

Chase squirts some oil into his palms and rubs his hands together. "I'll start here, alright?" He asks as he spreads that glistening oil over Max's left pec. Max closes his eyes and tries to keep himself together, even though it's obvious from how he bites his lips that he's loving what it feels like to be worshipped by another stud. Wordlessly, things heat up between them as Max brings his own oiled hands to Chase's chest, rubbing downwards to his abs.

"Oh, that tickles!" Chase chuckles.

"I don't think you wanna let him know that," Max comments, nodding sideways at me, and we all laugh together at the straight absurdity of this situation. I'm so glad they're getting along so well and being such good sports about this. It's such a rare sight to see men allowing themselves to be open with each other like this.

Of course, they will be much, much more open with each other later. When they're done, I luxuriate in the sight of these two oiled, jacked studs shining like warm bronze statues, their faces tinged with heat, their bulges plump and ready for action. I feel my own engine rev up and get ready to go.

***

"Ffir, ffir!!!" Chase screams through his gag, spit trickling off his chin and adding even more shine to his twisting oiled abs.

"Oh, you can do better than that," I taunt, pumping his dick energetically until I feel that deadly throb in the base of his cock when I finally let go. Chase's torso seizes up as his cock twitches like it's being shocked, all his core muscles clenching for dear life. It flings itself upwards a few times, wrestling against the load dammed up behind it.

Meanwhile, Max squirms beside him. I edged him first. Now, I'm keeping him on a low simmer with a vibrating cock ring as I rub Chase to boiling point too.

Good. Now I have two boys at 8/10.

"I've been edging you boys one by one. Now, I'm going to make you play together."

Chase and Max shiver as I shift them onto their feet by their cocks.

"Come on. Into the milking den."

Its main setup today is two chairs facing each other, with just enough space for one person to kneel between them. As we all settle into our positions, I feel so lucky to get to service these two kings. By themselves, I was already drowning in their manly majesty... more so now.

Chase and Max's wrists are strapped firmly to the backs of their chairs, and their ankles to the chairs' legs. Black straps fasten their thighs open for me and sink into their pecs, making them pop like glazed buns. Their hard, wet cocks dangle helplessly like ripe fruit to be plucked and juiced.

***

GAMES TO PLAY WITH BOUND BOYS: RELAY RACE

My palms slide up and down Chase and Max's cocks with slow, lazy strokes, just to keep them warm and ready to shoot. Chase is luxuriating in the tender waves of pleasure flowing through his loins; Max is keeping his core tight in case.

This is going to make my first game so fun.

"I'm going to stroke one of you until he's right about to burst. When you're there, you shout, 'pass!' Then, I'll move over to the next guy until he can't take it anymore, and then he tells me to pass it on. The rule: don't cum."

My boys share a chilling glance. They have to fight each other for their right to cum and damn the other to a long, long punishment.

Max stiffens even more than I thought he could.

"Max, you're up."

It doesn't take much to make Max go from warm to boiling hot. Well lubed up and already teased to bursting just a matter of minutes ago, I have him grunting and thrusting like a begging dog after a handful of relays back and forth.

"Pass!" Max shouts, his muscles shaking. I give him one last stroke across the head just to be sure before plunging down onto Chase's cock, cupping him up with my two hands as he moans in enjoyment. If he's moaning so intensely now, his chances are slim. Max catches his breath as he stares on hungrily at the torture I'm inflicting on Chase. I'm fondling his balls while pumping his cock like I'm churning butter. Chase screams and yelps as the pleasure gets almost too much to bear, and the thing is, I know exactly what too much looks like on his body. And I know that he's chickening out too quickly.

"Don't lie to me, Chase." Chase whimpers as I drive my palm down on his cock. "I spent one whole week edging you. I know you can hold it in much longer." Chase squeezes his eyes shut and howls as the ache boiling at the base of his cock sharpens and ignites, finally bringing honesty to his pleading, and as his chest contracts in shock I let go of him right on the precipice of an orgasm.

Chase almost weeps in relief as he feels that wave die down within him. Max heaves with a huge breath. He is close, but not dancing on tiptoes to keep it in yet. Reaching over to grab two cocks at once, I pump on both, and both boys moan in swelling bliss, but one of them has much more to lose.

"Argh, fuck, no!" Chase's voice snaps in desperation, straining up into a strangled scream as he realizes that he's been cornered. He's been pushed past the point of no return. And, clench as he might and squeeze all he can, he cannot stop the semen shooting up his hard abused cock.

A spurt of cum jets out of his penis.

Max roars like a football player who's scored a goal and Chase screams in utter defeat. I let go of his cock so that all he tastes is a whisper of pleasure, just the onset of an orgasm, his long agonizing build-up ruined but wanting more. His face is torn between frustration and fear. He knows that he's committed an unforgivable sin. He came without permission. Nothing but swift and humbling punishment lies on his horizon.

"Clever boy, Max! And bad, bad boy, Chase. I had one rule and you broke it. And I spent so much time training you." Chase sniffles as he stares down at his defiant dick, still twitching as a thin stream of cum leaks from it.

"Please, sir... it wasn't a full orgasm. You ruined it. You let go just as I started to cum. Please, I'll be good. I'll dance for you, anything, please!"

Drunk on his abject surrender, I stuff his gag back into his mouth.

"You deserve to be punished. You deserve to be fucked in the ass."

***

The seat of a man's soul is in his ass.

Chase's butt cheeks slap against each other as a robot dildo rams up into him, sending jackhammer pulses through his body, radiating out from his glowing prostate.

"Hnngh... hnggh!"

He's gagged and leaking from his mouth and cock, and tears well up in his eyes. It's pleasure so profoundly seismic that it exceeds the container of his body, so strong it's almost pain.

It's been ten minutes of watching Chase get his ass rammed inside out with my thrusting toy at full speed.

"That's what you get for being a bad boy," I call out over the thrusting and grunts. "But you - you've been good, haven't you, Max? Have you been a good boy for daddy?" I coo as I fan my fingers over Max's chest silkily. He's laid out on my lap like a stretching cat, his wrists bound over his head and his cock in my other hand. While Chase is getting pounded fast and painfully, I'm letting Max enjoy my slow, satin strokes. He looks like he's trying not to sink into a sweet, deep nap; his face is strained in the tension between surrender and containment. He's also looking over at Chase curiously.

A strained cry interrupts Max's sweet cooing - Chase is getting another ruined load milked out from his dry but unquenched cock. Thick white cum dribbles out impotently, the ghost of what could've been a good, juicy orgasm.

Chase's face is stricken with panic.

"I'm hawhry!" He cries, leaking even more drool from his gag, as his abs flex and try squeezing out as much pleasure as he can from that sour spurt.

As Chase heaves in exhaustion and shame, I switch off the dildo and stand before him for a bit, admiring the state of this man. I can smell his failure, see his labour dripping off his muscles.

"That's your punishment for cumming without permission. You wanted to cum, so I made you do it again. Are you going to work hard from now on?"

Chase nods obediently like a schoolboy and I ruffle his messy sweaty hair.

***

GAMES TO PLAY WITH BOUND BOYS: CHICKEN

Since Chase lost the first game, he starts in the receiving position: tied to the bed and blindfolded. Max leans by the side, waiting, drinking in the sight of Chase's body.

"Next game. Chase: your job is to not moan out loud. Max: your job is to make him moan and beg. Later, we switch. The guy who makes his prisoner chicken out and moan in the shortest time wins."

Chase squirms helplessly, and Max surveys his prey. Straight as he might say he is, the idea of conquering another man and torturing him with sex makes him feel strong and mighty.

"There's just one catch, Max."

Max's warm eyes tense up. He knew this was too good to be true and bites his lip as I hold out a small cardboard box with a hand-sized slit in its cover.

"Pick a card."

Max drags himself towards me. I might as well have asked him to pick the dildo I want to fuck him with. Blushing, Max reaches a strong hand into my box and pulls out a white card. His eyes scan it and what he reads makes him squirm:

"You can't use your hands."

But is he squirming out of awkwardness or anticipation? Max laughs nervously. I know, from the way he buzzes and from that plumping bulge, that part of that nervousness is glee.

"Go on. You know you want it," I goad and smack his ass playfully.

Slowly, like Adam and the forbidden fruit, Max approaches Chase's bound and exposed frame from the side. "I'm sorry, bro," he whispers into Chase's ear. "No hard feelings, okay?" Chase laughs resignedly.

And then, Max bends over Chase's shoulder and nuzzles Chase's neck.

Chase holds his breath. This is easy.

Max needs to go harder. He needs to break Chase if he wants to cum himself. He needs to let go of his ego, abandon his conformity to straightness. Steeling himself and pushing his own pride out the window, Max grazes Chase's neck with the tip of his tongue.