The Milking Den Ch. 09: Chase Meets Max

“Well done, Max. Now, let’s switch over.”

Max is blindfolded and strapped down to the bed, and Chase is driven by the need to redeem himself and a hunger for revenge. He draws his card from the box and it says…

“You can only use your bulge.”

Swollen with lust and competition, Chase snags a bottle of oil from the side table and climbs on top of his quarry.

“Dude, I’m going to make you moan so bad.”

Chase unscrews the bottle and pours glugs of oil all over Max like he’s watering a garden. Max digs his head into the bed as he feels the slick, thick oil ooze and leak all over his body. He shines so brightly it looks like he’s made of diamond. He wishes he can see himself.

Having already had his pride totally broken by getting fucked in the ass to a ruined orgasm, Chase goes straight for the kill – he straddles Max like a stallion and rubs his own crotch against Max’s bulge. Max’s voice catches in his throat as he gurgles with repressed pleasure. The oil intensifies all his senses; as Chase rubs not just his bulge but his entire body against Max, it feels like Max is sliding in and out of a huge pleasure sleeve. Max writhes in sex overload but manages to cough out a taunt –

“You can’t break me!”

Which only makes Chase thrust even harder, and makes me want to get involved too.

“Chase, you can use anything now.”

Chase smiles at me like a hound out for blood. Leering gruffly down at Max, he wraps his muscled, oiled body all around him, thrusting bulge to bulge, his tongue licking up a storm against Max’s neck, his fingers rubbing and twisting Max’s nipples. Swollen like ripe fruit, Max finally bursts. His mouth explodes in a stream of moans and gasps.

“Oh… oh! Fuck, I’m sorry!”

Three minutes and seventeen seconds!

“Chase, you win!” I shout over Max’s begging. He hasn’t stopped; he’s still going, rubbing his victory into Max’s soaked crotch. “I’ll just let you enjoy your victory for a while.”

“Oh oh! Please, you win… stop!” Max pleads, barely catching his breath between sharp moans and shouts. He can’t believe Chase feels so good on top of him – he almost doesn’t want it to stop.

Chase continues humping and ravishing Max as the boy wrestles futilely against his bonds. Part of it is enjoyment. Part of it is that feral urge to make his sub suffer. I let Chase continue to feast on shaking, begging Max as I set up the thrusting dildo.

***

Rest time. Well, for me. Chase and Max are getting to know each other very well. They kneel with their thighs woven between each other, tied hip to hip and chest to chest, their mouths gagged by a peeled banana stuffed both ways. They shine like bronze Roman statues. They have nowhere to look but each other’s eyes.

“Remember, first one to cause the banana to drop gets fucked again.”

Chase and Max exchange a desperate glance. Enemies or not, they have to work together, but one of them will be punished again. Max got it once. Chase has gotten it twice. Both of them are spent but not satisfied. It’s been twenty minutes. Their jaws are sore and red.

And then, something starts vibrating in their briefs.

Chase has already been through so much. That’s why his body is so sensitive, so easy to bend and break; the tremors send pleasure waves quaking through his groin and he wriggles in pleasure, biting into the banana and sending it tumbling off his shoulder and to the floor. Stricken with the realization that he was, again, to get fucked in the ass until he leaks, he collapses onto Max and sniffles.

***

Jazz music plays sultrily in the background as Chase struggles in his chair, a larger dildo fucking him to the rhythm. I stroke his dick, stopping right as another ruined load dribbles out of his cock, as Max helps me out by strumming Chase’s nipples. Chase’s face is red with bliss and frustration.

“So, Max, still think you’re straight?”

Max laughs, his eyes twinkling. He’s realized he loves the feel of nipples and oily muscles.

“Aww, that’s nice. Come on, don’t you wanna thank Chase for helping you discover that?”

“My pleasure.” And he bends over to lick Chase’s tender neck as I polish Chase’s sensitive spent cockhead. Chase barely struggles any more.

***

THE GRAND FINALE: COCKFIGHT

Butt fuck ruined orgasm tally: Chase 3, Max 1.

Both of them are sore and broken all over, but their cocks – drained as they might be – are still desperate for one good orgasm.

And from the way I’ve set them up, they have a good idea how this night will end.

Chase and Max stand on a spread-out tarp that has been covered in lube, just like they are. They face each other like boxers in a ring. Their brows are set and their cocks are hard.

This is going to be good.

“Your job is to make the other guy cum first. Whoever cums first, loses. Your punishment: getting fucked both ways for an hour.” I gesture to the traumatic set-up that both of them know so well – a kneeling pad with a rubber sucker in front and a thruster behind.

“No rules, no time limit. Enjoy.”

I sit back and await the show.

Thoroughly inflamed with red hot animal lust, Chase and Max charge at each other like bulls. They wrestle each other all over the floor, rolling around in lube. Chase fights bravely, but his three ruined orgasms have weakened him so much that Max crawls on top of him without much of a fight. Max pins Chase down with his thick thighs, dips his hands into the lube on the mat, and jerks Chase’s cock hard like a jackhammer.

“Fuck, stop it!” Chase roars. He slaps his hands on Max’s chest and flicks his nipples, loosening Max’s resolve as ticklish pleasure floods his body from his nipples. As Max loosens, Chase slides out from underneath Max’s legs and grapples him, reaching for his cock and jerking it too.

Chase screams gutturally – pleasure is building up in his cock, swelling towards the point of no return. “Please, bro, I really can’t take the punishment. Please,” Chase begs, his eyes round and big like a sad puppy. Someone like Chase simply can’t lie. He’s so genuine about this – his ass is so sore and his cock so drained that one hour of punishment would destroy him.

“I’m sorry, dude. I’m not getting fucked again!” Max grunts even though his eyes are soft with compassion. He pushes that thought out of his head and turns his gaze sharp and hot, drilling down into Chase potently as his fist continues pounding Chase’s cock. Both men jerk each other off, their tongues lashing in pleasure and torture as they swell together. Their chests heave and their abs contract, their slippery bodies torched with pleasure.

“Oh my god. Wait. Stop. Stop, stop.” Chase breaks character, his eyes wide with an idea. Max looks down at him confused. “What if we cum together? Then nobody loses and we both win.”

Drunk on lust, Max nods feverishly. His cock hardens visibly at the idea of finally getting off guilt-free. “Fuck, yes. Let’s do it.”

They look at me and I shrug.

Chase and Max rub up against each other again, but this time, it’s not a fight of strength and virility. Their muscles push and their fists pump not in combat, but cooperation. As they wrestle, they converge. The heat melts and melds them together in hot, sweaty lust.

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